diff --git a/apps/desktop/desktop_native/macos_provider/src/assertion.rs b/apps/desktop/desktop_native/macos_provider/src/assertion.rs
index 762ceaaed48..c5b43bb87fa 100644
--- a/apps/desktop/desktop_native/macos_provider/src/assertion.rs
+++ b/apps/desktop/desktop_native/macos_provider/src/assertion.rs
@@ -2,11 +2,22 @@ use std::sync::Arc;
 
 use serde::{Deserialize, Serialize};
 
-use crate::{BitwardenError, Callback, UserVerification};
+use crate::{BitwardenError, Callback, Position, UserVerification};
 
 #[derive(uniffi::Record, Debug, Serialize, Deserialize)]
 #[serde(rename_all = "camelCase")]
 pub struct PasskeyAssertionRequest {
+    rp_id: String,
+    client_data_hash: Vec<u8>,
+    user_verification: UserVerification,
+    allowed_credentials: Vec<Vec<u8>>,
+    window_xy: Position,
+    //extension_input: Vec<u8>, TODO: Implement support for extensions
+}
+
+#[derive(uniffi::Record, Debug, Serialize, Deserialize)]
+#[serde(rename_all = "camelCase")]
+pub struct PasskeyAssertionWithoutUserInterfaceRequest {
     rp_id: String,
     credential_id: Vec<u8>,
     user_name: String,
@@ -14,6 +25,7 @@ pub struct PasskeyAssertionRequest {
     record_identifier: Option<String>,
     client_data_hash: Vec<u8>,
     user_verification: UserVerification,
+    window_xy: Position,
 }
 
 #[derive(uniffi::Record, Serialize, Deserialize)]
diff --git a/apps/desktop/desktop_native/macos_provider/src/lib.rs b/apps/desktop/desktop_native/macos_provider/src/lib.rs
index 5623436d874..8f2499ae68d 100644
--- a/apps/desktop/desktop_native/macos_provider/src/lib.rs
+++ b/apps/desktop/desktop_native/macos_provider/src/lib.rs
@@ -15,7 +15,10 @@ uniffi::setup_scaffolding!();
 mod assertion;
 mod registration;
 
-use assertion::{PasskeyAssertionRequest, PreparePasskeyAssertionCallback};
+use assertion::{
+    PasskeyAssertionRequest, PasskeyAssertionWithoutUserInterfaceRequest,
+    PreparePasskeyAssertionCallback,
+};
 use registration::{PasskeyRegistrationRequest, PreparePasskeyRegistrationCallback};
 
 #[derive(uniffi::Enum, Debug, Serialize, Deserialize)]
@@ -26,6 +29,13 @@ pub enum UserVerification {
     Discouraged,
 }
 
+#[derive(uniffi::Record, Debug, Serialize, Deserialize)]
+#[serde(rename_all = "camelCase")]
+pub struct Position {
+    pub x: i32,
+    pub y: i32,
+}
+
 #[derive(Debug, uniffi::Error, Serialize, Deserialize)]
 pub enum BitwardenError {
     Internal(String),
@@ -141,6 +151,14 @@ impl MacOSProviderClient {
     ) {
         self.send_message(request, Box::new(callback));
     }
+
+    pub fn prepare_passkey_assertion_without_user_interface(
+        &self,
+        request: PasskeyAssertionWithoutUserInterfaceRequest,
+        callback: Arc<dyn PreparePasskeyAssertionCallback>,
+    ) {
+        self.send_message(request, Box::new(callback));
+    }
 }
 
 #[derive(Serialize, Deserialize)]
diff --git a/apps/desktop/desktop_native/macos_provider/src/registration.rs b/apps/desktop/desktop_native/macos_provider/src/registration.rs
index d484af58b6c..9e697b75c16 100644
--- a/apps/desktop/desktop_native/macos_provider/src/registration.rs
+++ b/apps/desktop/desktop_native/macos_provider/src/registration.rs
@@ -2,7 +2,7 @@ use std::sync::Arc;
 
 use serde::{Deserialize, Serialize};
 
-use crate::{BitwardenError, Callback, UserVerification};
+use crate::{BitwardenError, Callback, Position, UserVerification};
 
 #[derive(uniffi::Record, Debug, Serialize, Deserialize)]
 #[serde(rename_all = "camelCase")]
@@ -13,6 +13,7 @@ pub struct PasskeyRegistrationRequest {
     client_data_hash: Vec<u8>,
     user_verification: UserVerification,
     supported_algorithms: Vec<i32>,
+    window_xy: Position,
 }
 
 #[derive(uniffi::Record, Serialize, Deserialize)]
diff --git a/apps/desktop/desktop_native/napi/index.d.ts b/apps/desktop/desktop_native/napi/index.d.ts
index 92f31cf5f89..ca1fe29e254 100644
--- a/apps/desktop/desktop_native/napi/index.d.ts
+++ b/apps/desktop/desktop_native/napi/index.d.ts
@@ -118,6 +118,10 @@ export declare namespace autofill {
     Required = 'required',
     Discouraged = 'discouraged'
   }
+  export interface Position {
+    x: number
+    y: number
+  }
   export interface PasskeyRegistrationRequest {
     rpId: string
     userName: string
@@ -125,6 +129,7 @@ export declare namespace autofill {
     clientDataHash: Array<number>
     userVerification: UserVerification
     supportedAlgorithms: Array<number>
+    windowXy: Position
   }
   export interface PasskeyRegistrationResponse {
     rpId: string
@@ -133,6 +138,13 @@ export declare namespace autofill {
     attestationObject: Array<number>
   }
   export interface PasskeyAssertionRequest {
+    rpId: string
+    clientDataHash: Array<number>
+    userVerification: UserVerification
+    allowedCredentials: Array<Array<number>>
+    windowXy: Position
+  }
+  export interface PasskeyAssertionWithoutUserInterfaceRequest {
     rpId: string
     credentialId: Array<number>
     userName: string
@@ -140,6 +152,7 @@ export declare namespace autofill {
     recordIdentifier?: string
     clientDataHash: Array<number>
     userVerification: UserVerification
+    windowXy: Position
   }
   export interface PasskeyAssertionResponse {
     rpId: string
@@ -156,7 +169,7 @@ export declare namespace autofill {
      * @param name The endpoint name to listen on. This name uniquely identifies the IPC connection and must be the same for both the server and client.
      * @param callback This function will be called whenever a message is received from a client.
      */
-    static listen(name: string, registrationCallback: (error: null | Error, clientId: number, sequenceNumber: number, message: PasskeyRegistrationRequest) => void, assertionCallback: (error: null | Error, clientId: number, sequenceNumber: number, message: PasskeyAssertionRequest) => void): Promise<IpcServer>
+    static listen(name: string, registrationCallback: (error: null | Error, clientId: number, sequenceNumber: number, message: PasskeyRegistrationRequest) => void, assertionCallback: (error: null | Error, clientId: number, sequenceNumber: number, message: PasskeyAssertionRequest) => void, assertionWithoutUserInterfaceCallback: (error: null | Error, clientId: number, sequenceNumber: number, message: PasskeyAssertionWithoutUserInterfaceRequest) => void): Promise<IpcServer>
     /** Return the path to the IPC server. */
     getPath(): string
     /** Stop the IPC server. */
diff --git a/apps/desktop/desktop_native/napi/src/lib.rs b/apps/desktop/desktop_native/napi/src/lib.rs
index d0c859d427c..f02be2b27b6 100644
--- a/apps/desktop/desktop_native/napi/src/lib.rs
+++ b/apps/desktop/desktop_native/napi/src/lib.rs
@@ -515,6 +515,14 @@ pub mod autofill {
         pub value: Result<T, BitwardenError>,
     }
 
+    #[napi(object)]
+    #[derive(Debug, Serialize, Deserialize)]
+    #[serde(rename_all = "camelCase")]
+    pub struct Position {
+        pub x: i32,
+        pub y: i32,
+    }
+
     #[napi(object)]
     #[derive(Debug, Serialize, Deserialize)]
     #[serde(rename_all = "camelCase")]
@@ -525,6 +533,7 @@ pub mod autofill {
         pub client_data_hash: Vec<u8>,
         pub user_verification: UserVerification,
         pub supported_algorithms: Vec<i32>,
+        pub window_xy: Position,
     }
 
     #[napi(object)]
@@ -541,6 +550,18 @@ pub mod autofill {
     #[derive(Debug, Serialize, Deserialize)]
     #[serde(rename_all = "camelCase")]
     pub struct PasskeyAssertionRequest {
+        pub rp_id: String,
+        pub client_data_hash: Vec<u8>,
+        pub user_verification: UserVerification,
+        pub allowed_credentials: Vec<Vec<u8>>,
+        pub window_xy: Position,
+        //extension_input: Vec<u8>, TODO: Implement support for extensions
+    }
+
+    #[napi(object)]
+    #[derive(Debug, Serialize, Deserialize)]
+    #[serde(rename_all = "camelCase")]
+    pub struct PasskeyAssertionWithoutUserInterfaceRequest {
         pub rp_id: String,
         pub credential_id: Vec<u8>,
         pub user_name: String,
@@ -548,6 +569,7 @@ pub mod autofill {
         pub record_identifier: Option<String>,
         pub client_data_hash: Vec<u8>,
         pub user_verification: UserVerification,
+        pub window_xy: Position,
     }
 
     #[napi(object)]
@@ -592,6 +614,13 @@ pub mod autofill {
                 (u32, u32, PasskeyAssertionRequest),
                 ErrorStrategy::CalleeHandled,
             >,
+            #[napi(
+                ts_arg_type = "(error: null | Error, clientId: number, sequenceNumber: number, message: PasskeyAssertionWithoutUserInterfaceRequest) => void"
+            )]
+            assertion_without_user_interface_callback: ThreadsafeFunction<
+                (u32, u32, PasskeyAssertionWithoutUserInterfaceRequest),
+                ErrorStrategy::CalleeHandled,
+            >,
         ) -> napi::Result<Self> {
             let (send, mut recv) = tokio::sync::mpsc::channel::<Message>(32);
             tokio::spawn(async move {
@@ -628,6 +657,25 @@ pub mod autofill {
                                 }
                             }
 
+                            match serde_json::from_str::<
+                                PasskeyMessage<PasskeyAssertionWithoutUserInterfaceRequest>,
+                            >(&message)
+                            {
+                                Ok(msg) => {
+                                    let value = msg
+                                        .value
+                                        .map(|value| (client_id, msg.sequence_number, value))
+                                        .map_err(|e| napi::Error::from_reason(format!("{e:?}")));
+
+                                    assertion_without_user_interface_callback
+                                        .call(value, ThreadsafeFunctionCallMode::NonBlocking);
+                                    continue;
+                                }
+                                Err(e) => {
+                                    println!("[ERROR] Error deserializing message1: {e}");
+                                }
+                            }
+
                             match serde_json::from_str::<PasskeyMessage<PasskeyRegistrationRequest>>(
                                 &message,
                             ) {
diff --git a/apps/desktop/macos/autofill-extension/Base.lproj/CredentialProviderViewController.xib b/apps/desktop/macos/autofill-extension/Base.lproj/CredentialProviderViewController.xib
index ace3497a58b..1e47cc54de2 100644
--- a/apps/desktop/macos/autofill-extension/Base.lproj/CredentialProviderViewController.xib
+++ b/apps/desktop/macos/autofill-extension/Base.lproj/CredentialProviderViewController.xib
@@ -1,22 +1,23 @@
 <?xml version="1.0" encoding="UTF-8"?>
-<document type="com.apple.InterfaceBuilder3.Cocoa.XIB" version="3.0" toolsVersion="17021" targetRuntime="MacOSX.Cocoa" propertyAccessControl="none" useAutolayout="YES" customObjectInstantitationMethod="direct">
+<document type="com.apple.InterfaceBuilder3.Cocoa.XIB" version="3.0" toolsVersion="23504" targetRuntime="MacOSX.Cocoa" propertyAccessControl="none" useAutolayout="YES" customObjectInstantitationMethod="direct">
     <dependencies>
-        <plugIn identifier="com.apple.InterfaceBuilder.CocoaPlugin" version="17021"/>
+        <deployment identifier="macosx"/>
+        <plugIn identifier="com.apple.InterfaceBuilder.CocoaPlugin" version="23504"/>
         <capability name="documents saved in the Xcode 8 format" minToolsVersion="8.0"/>
     </dependencies>
     <objects>
-        <customObject id="-2" userLabel="File's Owner" customClass="CredentialProviderViewController" customModuleProvider="target">
+        <customObject id="-2" userLabel="File's Owner" customClass="CredentialProviderViewController" customModule="autofill_extension" customModuleProvider="target">
             <connections>
                 <outlet property="view" destination="1" id="2"/>
             </connections>
         </customObject>
         <customObject id="-1" userLabel="First Responder" customClass="FirstResponder"/>
         <customObject id="-3" userLabel="Application" customClass="NSObject"/>
-        <customView translatesAutoresizingMaskIntoConstraints="NO" id="1">
+        <customView hidden="YES" translatesAutoresizingMaskIntoConstraints="NO" id="1">
             <rect key="frame" x="0.0" y="0.0" width="378" height="94"/>
             <subviews>
                 <button verticalHuggingPriority="750" translatesAutoresizingMaskIntoConstraints="NO" id="1uM-r7-H1c">
-                    <rect key="frame" x="177" y="3" width="197" height="32"/>
+                    <rect key="frame" x="184" y="3" width="191" height="32"/>
                     <buttonCell key="cell" type="push" title="Return Example Password" bezelStyle="rounded" alignment="center" borderStyle="border" imageScaling="proportionallyDown" inset="2" id="2l4-PO-we5">
                         <behavior key="behavior" pushIn="YES" lightByBackground="YES" lightByGray="YES"/>
                         <font key="font" metaFont="system"/>
@@ -28,10 +29,7 @@
                     </connections>
                 </button>
                 <button verticalHuggingPriority="750" translatesAutoresizingMaskIntoConstraints="NO" id="NVE-vN-dkz">
-                    <rect key="frame" x="99" y="3" width="82" height="32"/>
-                    <constraints>
-                        <constraint firstAttribute="width" relation="greaterThanOrEqual" constant="60" id="cP1-hK-9ZX"/>
-                    </constraints>
+                    <rect key="frame" x="114" y="3" width="76" height="32"/>
                     <buttonCell key="cell" type="push" title="Cancel" bezelStyle="rounded" alignment="center" borderStyle="border" imageScaling="proportionallyDown" inset="2" id="6Up-t3-mwm">
                         <behavior key="behavior" pushIn="YES" lightByBackground="YES" lightByGray="YES"/>
                         <font key="font" metaFont="system"/>
@@ -39,13 +37,16 @@
 Gw
 </string>
                     </buttonCell>
+                    <constraints>
+                        <constraint firstAttribute="width" relation="greaterThanOrEqual" constant="60" id="cP1-hK-9ZX"/>
+                    </constraints>
                     <connections>
                         <action selector="cancel:" target="-2" id="Qav-AK-DGt"/>
                     </connections>
                 </button>
                 <textField verticalHuggingPriority="750" translatesAutoresizingMaskIntoConstraints="NO" id="aNc-0i-CWK">
-                    <rect key="frame" x="135" y="63" width="108" height="16"/>
-                    <textFieldCell key="cell" scrollable="YES" lineBreakMode="clipping" sendsActionOnEndEditing="YES" alignment="left" title="autofill-extension" id="0xp-rC-2gr">
+                    <rect key="frame" x="112" y="63" width="154" height="16"/>
+                    <textFieldCell key="cell" scrollable="YES" lineBreakMode="clipping" sendsActionOnEndEditing="YES" alignment="left" title="autofill-extension hello" id="0xp-rC-2gr">
                         <font key="font" metaFont="systemBold"/>
                         <color key="textColor" name="controlTextColor" catalog="System" colorSpace="catalog"/>
                         <color key="backgroundColor" name="controlColor" catalog="System" colorSpace="catalog"/>
diff --git a/apps/desktop/macos/autofill-extension/CredentialProviderViewController.swift b/apps/desktop/macos/autofill-extension/CredentialProviderViewController.swift
index dbaa8517086..5568b2e75db 100644
--- a/apps/desktop/macos/autofill-extension/CredentialProviderViewController.swift
+++ b/apps/desktop/macos/autofill-extension/CredentialProviderViewController.swift
@@ -17,17 +17,56 @@ class CredentialProviderViewController: ASCredentialProviderViewController {
     //
     // If instead I make this a static, the deinit gets called correctly after each request.
     // I think we still might want a static regardless, to be able to reuse the connection if possible.
-    static let client: MacOsProviderClient = {
-        let instance = MacOsProviderClient.connect()
-         // setup code
-         return instance
-     }()
+    let client: MacOsProviderClient = {
+        let logger = Logger(subsystem: "com.bitwarden.desktop.autofill-extension", category: "credential-provider")
+        
+        // Check if the Electron app is running
+        let workspace = NSWorkspace.shared
+        let isRunning = workspace.runningApplications.contains { app in
+            app.bundleIdentifier == "com.bitwarden.desktop"
+        }
+        
+        if !isRunning {
+           logger.log("[autofill-extension] Bitwarden Desktop not running, attempting to launch")
+            
+           // Try to launch the app
+            if let appURL = workspace.urlForApplication(withBundleIdentifier: "com.bitwarden.desktop") {
+                let semaphore = DispatchSemaphore(value: 0)
+                
+                workspace.openApplication(at: appURL,
+                                          configuration: NSWorkspace.OpenConfiguration()) { app, error in
+                    if let error = error {
+                        logger.error("[autofill-extension] Failed to launch Bitwarden Desktop: \(error.localizedDescription)")
+                    } else if let app = app {
+                        logger.log("[autofill-extension] Successfully launched Bitwarden Desktop")
+                    } else {
+                        logger.error("[autofill-extension] Failed to launch Bitwarden Desktop: unknown error")
+                    }
+                    semaphore.signal()
+                }
+                
+                // Wait for launch completion with timeout
+                _ = semaphore.wait(timeout: .now() + 5.0)
+                
+                // Add a small delay to allow for initialization
+                Thread.sleep(forTimeInterval: 1.0)
+            } else {
+                logger.error("[autofill-extension] Could not find Bitwarden Desktop app")
+            }
+        } else {
+            logger.log("[autofill-extension] Bitwarden Desktop is running")    
+        }
+        
+        logger.log("[autofill-extension] Connecting to Bitwarden over IPC")    
+
+        return MacOsProviderClient.connect()
+    }()
     
     init() {
         logger = Logger(subsystem: "com.bitwarden.desktop.autofill-extension", category: "credential-provider")
         
         logger.log("[autofill-extension] initializing extension")
-
+        
         super.init(nibName: nil, bundle: nil)
     }
     
@@ -43,40 +82,35 @@ class CredentialProviderViewController: ASCredentialProviderViewController {
     @IBAction func cancel(_ sender: AnyObject?) {
         self.extensionContext.cancelRequest(withError: NSError(domain: ASExtensionErrorDomain, code: ASExtensionError.userCanceled.rawValue))
     }
-
+    
     @IBAction func passwordSelected(_ sender: AnyObject?) {
         let passwordCredential = ASPasswordCredential(user: "j_appleseed", password: "apple1234")
         self.extensionContext.completeRequest(withSelectedCredential: passwordCredential, completionHandler: nil)
     }
     
-    /*
-     Implement this method if your extension supports showing credentials in the QuickType bar.
-     When the user selects a credential from your app, this method will be called with the
-     ASPasswordCredentialIdentity your app has previously saved to the ASCredentialIdentityStore.
-     Provide the password by completing the extension request with the associated ASPasswordCredential.
-     If using the credential would require showing custom UI for authenticating the user, cancel
-     the request with error code ASExtensionError.userInteractionRequired.
-
-     */
-
-    // Deprecated
-    override func provideCredentialWithoutUserInteraction(for credentialIdentity: ASPasswordCredentialIdentity) {
-        logger.log("[autofill-extension] provideCredentialWithoutUserInteraction called \(credentialIdentity)")
-        logger.log("[autofill-extension]     user \(credentialIdentity.user)")
-        logger.log("[autofill-extension]     id \(credentialIdentity.recordIdentifier ?? "")")
-        logger.log("[autofill-extension]     sid \(credentialIdentity.serviceIdentifier.identifier)")
-        logger.log("[autofill-extension]     sidt \(credentialIdentity.serviceIdentifier.type.rawValue)")
+    private func getWindowPosition() -> Position {
+        let frame = self.view.window?.frame ?? .zero
+        let screenHeight = NSScreen.main?.frame.height ?? 0      
         
-//        let databaseIsUnlocked = true
-//        if (databaseIsUnlocked) {
-        let passwordCredential = ASPasswordCredential(user: credentialIdentity.user, password: "example1234")
-            self.extensionContext.completeRequest(withSelectedCredential: passwordCredential, completionHandler: nil)
-//        } else {
-//            self.extensionContext.cancelRequest(withError: NSError(domain: ASExtensionErrorDomain, code:ASExtensionError.userInteractionRequired.rawValue))
-//        }
+        // frame.width and frame.height is always 0. Estimating works OK for now.
+        let estimatedWidth:CGFloat = 400;
+        let estimatedHeight:CGFloat = 200;
+        let centerX = Int32(round(frame.origin.x + estimatedWidth/2))
+        let centerY = Int32(round(screenHeight - (frame.origin.y + estimatedHeight/2)))
+        
+        return Position(x: centerX, y:centerY)
     }
     
+    override func loadView() {
+        let view = NSView()
+        // Hide the native window since we only need the IPC connection
+        view.isHidden = true    
+        self.view = view
+    }
+       
     override func provideCredentialWithoutUserInteraction(for credentialRequest: any ASCredentialRequest) {
+        let timeoutTimer = createTimer()
+
         if let request = credentialRequest as? ASPasskeyCredentialRequest {
             if let passkeyIdentity = request.credentialIdentity as? ASPasskeyCredentialIdentity {
                 
@@ -84,11 +118,16 @@ class CredentialProviderViewController: ASCredentialProviderViewController {
                 
                 class CallbackImpl: PreparePasskeyAssertionCallback {
                     let ctx: ASCredentialProviderExtensionContext
-                    required init(_ ctx: ASCredentialProviderExtensionContext) {
+                    let logger: Logger
+                    let timeoutTimer: DispatchWorkItem
+                    required init(_ ctx: ASCredentialProviderExtensionContext,_ logger: Logger, _ timeoutTimer: DispatchWorkItem) {
                         self.ctx = ctx
+                        self.logger = logger
+                        self.timeoutTimer = timeoutTimer
                     }
                     
                     func onComplete(credential: PasskeyAssertionResponse) {
+                        self.timeoutTimer.cancel()
                         ctx.completeAssertionRequest(using: ASPasskeyAssertionCredential(
                             userHandle: credential.userHandle,
                             relyingParty: credential.rpId,
@@ -100,6 +139,8 @@ class CredentialProviderViewController: ASCredentialProviderViewController {
                     }
                     
                     func onError(error: BitwardenError) {
+                        logger.error("[autofill-extension] OnError called, cancelling the request \(error)")
+                        self.timeoutTimer.cancel()
                         ctx.cancelRequest(withError: error)
                     }
                 }
@@ -113,55 +154,74 @@ class CredentialProviderViewController: ASCredentialProviderViewController {
                     UserVerification.discouraged
                 }
                 
-                let req = PasskeyAssertionRequest(
+                let req = PasskeyAssertionWithoutUserInterfaceRequest(
                     rpId: passkeyIdentity.relyingPartyIdentifier,
                     credentialId: passkeyIdentity.credentialID,
                     userName: passkeyIdentity.userName,
                     userHandle: passkeyIdentity.userHandle,
                     recordIdentifier: passkeyIdentity.recordIdentifier,
                     clientDataHash: request.clientDataHash,
-                    userVerification: userVerification
+                    userVerification: userVerification,
+                    windowXy: self.getWindowPosition()
                 )
                 
-                CredentialProviderViewController.client.preparePasskeyAssertion(request: req, callback: CallbackImpl(self.extensionContext))
+                self.client.preparePasskeyAssertionWithoutUserInterface(request: req, callback: CallbackImpl(self.extensionContext, self.logger, timeoutTimer))
                 return
             }
         }
         
-        if let request = credentialRequest as? ASPasswordCredentialRequest {
-            logger.log("[autofill-extension] provideCredentialWithoutUserInteraction2(password) called \(request)")
-            return;
-        }
-       
+        timeoutTimer.cancel()
+        
         logger.log("[autofill-extension] provideCredentialWithoutUserInteraction2 called wrong")
         self.extensionContext.cancelRequest(withError: BitwardenError.Internal("Invalid authentication request"))
     }
-
+    
     /*
      Implement this method if provideCredentialWithoutUserInteraction(for:) can fail with
      ASExtensionError.userInteractionRequired. In this case, the system may present your extension's
      UI and call this method. Show appropriate UI for authenticating the user then provide the password
      by completing the extension request with the associated ASPasswordCredential.
+     
+     override func prepareInterfaceToProvideCredential(for credentialIdentity: ASPasswordCredentialIdentity) {
+     }
+     */
 
-    override func prepareInterfaceToProvideCredential(for credentialIdentity: ASPasswordCredentialIdentity) {
-    }
-    */
+    private func createTimer() -> DispatchWorkItem {
+        // Create a timer for 600 second timeout
+        let timeoutTimer = DispatchWorkItem { [weak self] in
+            guard let self = self else { return }
+            logger.log("[autofill-extension] The operation timed out after 600 seconds")
+            self.extensionContext.cancelRequest(withError: BitwardenError.Internal("The operation timed out"))
+        }
+        
+        // Schedule the timeout
+        DispatchQueue.main.asyncAfter(deadline: .now() + 600, execute: timeoutTimer)
 
-
-    override func prepareInterfaceForExtensionConfiguration() {
-        logger.log("[autofill-extension] prepareInterfaceForExtensionConfiguration called")
+        return timeoutTimer
     }
 
     override func prepareInterface(forPasskeyRegistration registrationRequest: ASCredentialRequest) {
+        logger.log("[autofill-extension] prepareInterface")
+        let timeoutTimer = createTimer()
+
+        
         if let request = registrationRequest as? ASPasskeyCredentialRequest {
             if let passkeyIdentity = registrationRequest.credentialIdentity as? ASPasskeyCredentialIdentity {
+                logger.log("[autofill-extension] prepareInterface(passkey) called \(request)")
+                
                 class CallbackImpl: PreparePasskeyRegistrationCallback {
                     let ctx: ASCredentialProviderExtensionContext
-                    required init(_ ctx: ASCredentialProviderExtensionContext) {
+                    let timeoutTimer: DispatchWorkItem
+                    let logger: Logger
+                    
+                    required init(_ ctx: ASCredentialProviderExtensionContext, _ logger: Logger,_ timeoutTimer: DispatchWorkItem) {
                         self.ctx = ctx
+                        self.logger = logger
+                        self.timeoutTimer = timeoutTimer
                     }
-
+                    
                     func onComplete(credential: PasskeyRegistrationResponse) {
+                        self.timeoutTimer.cancel()
                         ctx.completeRegistrationRequest(using: ASPasskeyRegistrationCredential(
                             relyingParty: credential.rpId,
                             clientDataHash: credential.clientDataHash,
@@ -169,58 +229,99 @@ class CredentialProviderViewController: ASCredentialProviderViewController {
                             attestationObject: credential.attestationObject
                         ))
                     }
-
+                    
                     func onError(error: BitwardenError) {
+                        logger.error("[autofill-extension] OnError called, cancelling the request \(error)")
+                        self.timeoutTimer.cancel()
                         ctx.cancelRequest(withError: error)
                     }
                 }
                 
                 let userVerification = switch request.userVerificationPreference {
-                    case .preferred:
-                        UserVerification.preferred
-                    case .required:
-                        UserVerification.required
-                    default:
-                        UserVerification.discouraged
+                case .preferred:
+                    UserVerification.preferred
+                case .required:
+                    UserVerification.required
+                default:
+                    UserVerification.discouraged
                 }
-
+                
                 let req = PasskeyRegistrationRequest(
                     rpId: passkeyIdentity.relyingPartyIdentifier,
                     userName: passkeyIdentity.userName,
                     userHandle: passkeyIdentity.userHandle,
                     clientDataHash: request.clientDataHash,
                     userVerification: userVerification,
-                    supportedAlgorithms: request.supportedAlgorithms.map{ Int32($0.rawValue) }
+                    supportedAlgorithms: request.supportedAlgorithms.map{ Int32($0.rawValue) },
+                    windowXy: self.getWindowPosition()
                 )
-                CredentialProviderViewController.client.preparePasskeyRegistration(request: req, callback: CallbackImpl(self.extensionContext))
+                logger.log("[autofill-extension] prepareInterface(passkey) calling preparePasskeyRegistration")                
+                
+                self.client.preparePasskeyRegistration(request: req, callback: CallbackImpl(self.extensionContext, self.logger, timeoutTimer))
                 return
             }
         }
-
+        
+        logger.log("[autofill-extension] We didn't get a passkey")
+        
+        timeoutTimer.cancel()
         // If we didn't get a passkey, return an error
         self.extensionContext.cancelRequest(withError: BitwardenError.Internal("Invalid registration request"))
     }
-
-    /*
-      Prepare your UI to list available credentials for the user to choose from. The items in
-      'serviceIdentifiers' describe the service the user is logging in to, so your extension can
-      prioritize the most relevant credentials in the list.
-     */
-    override func prepareCredentialList(for serviceIdentifiers: [ASCredentialServiceIdentifier]) {
-        logger.log("[autofill-extension] prepareCredentialList for serviceIdentifiers: \(serviceIdentifiers.count)")
-
-        for serviceIdentifier in serviceIdentifiers {
-            logger.log("     service: \(serviceIdentifier.identifier)")
-        }
-    }
-
+    
     override func prepareCredentialList(for serviceIdentifiers: [ASCredentialServiceIdentifier], requestParameters: ASPasskeyCredentialRequestParameters) {
         logger.log("[autofill-extension] prepareCredentialList(passkey) for serviceIdentifiers: \(serviceIdentifiers.count)")
-        logger.log("request parameters: \(requestParameters.relyingPartyIdentifier)")
-        
-        for serviceIdentifier in serviceIdentifiers {
-            logger.log("     service: \(serviceIdentifier.identifier)")
+                               
+        class CallbackImpl: PreparePasskeyAssertionCallback {
+            let ctx: ASCredentialProviderExtensionContext
+            let timeoutTimer: DispatchWorkItem
+            let logger: Logger
+            required init(_ ctx: ASCredentialProviderExtensionContext,_ logger: Logger, _ timeoutTimer: DispatchWorkItem) {
+                self.ctx = ctx
+                self.logger = logger
+                self.timeoutTimer = timeoutTimer
+            }
+            
+            func onComplete(credential: PasskeyAssertionResponse) {
+                self.timeoutTimer.cancel()
+                ctx.completeAssertionRequest(using: ASPasskeyAssertionCredential(
+                    userHandle: credential.userHandle,
+                    relyingParty: credential.rpId,
+                    signature: credential.signature,
+                    clientDataHash: credential.clientDataHash,
+                    authenticatorData: credential.authenticatorData,
+                    credentialID: credential.credentialId
+                ))
+            }
+            
+            func onError(error: BitwardenError) {
+                logger.error("[autofill-extension] OnError called, cancelling the request \(error)")
+                self.timeoutTimer.cancel()
+                ctx.cancelRequest(withError: error)
+            }
         }
-    }
-
+        
+        let userVerification = switch requestParameters.userVerificationPreference {
+        case .preferred:
+            UserVerification.preferred
+        case .required:
+            UserVerification.required
+        default:
+            UserVerification.discouraged
+        }
+        
+        let req = PasskeyAssertionRequest(
+            rpId: requestParameters.relyingPartyIdentifier,
+            clientDataHash: requestParameters.clientDataHash,
+            userVerification: userVerification,
+            allowedCredentials: requestParameters.allowedCredentials,
+            windowXy: self.getWindowPosition()
+            //extensionInput: requestParameters.extensionInput,
+        )
+        
+        let timeoutTimer = createTimer()
+        
+        self.client.preparePasskeyAssertion(request: req, callback: CallbackImpl(self.extensionContext, self.logger, timeoutTimer))
+        return
+    }    
 }
diff --git a/apps/desktop/src/app/app-routing.module.ts b/apps/desktop/src/app/app-routing.module.ts
index 36e267c9355..3bb130d321d 100644
--- a/apps/desktop/src/app/app-routing.module.ts
+++ b/apps/desktop/src/app/app-routing.module.ts
@@ -182,6 +182,10 @@ const routes: Routes = [
     path: "passkeys",
     component: Fido2PlaceholderComponent,
   },
+  {
+    path: "passkeys",
+    component: Fido2PlaceholderComponent,
+  },
   {
     path: "",
     component: AnonLayoutWrapperComponent,
diff --git a/apps/desktop/src/app/components/fido2placeholder.component.ts b/apps/desktop/src/app/components/fido2placeholder.component.ts
index b3302d63241..b95dcc6d890 100644
--- a/apps/desktop/src/app/components/fido2placeholder.component.ts
+++ b/apps/desktop/src/app/components/fido2placeholder.component.ts
@@ -1,16 +1,45 @@
-import { Component } from "@angular/core";
+import { CommonModule } from "@angular/common";
+import { Component, OnDestroy, OnInit } from "@angular/core";
 import { Router } from "@angular/router";
+import { BehaviorSubject, Observable } from "rxjs";
 
+import {
+  DesktopFido2UserInterfaceService,
+  DesktopFido2UserInterfaceSession,
+} from "../../autofill/services/desktop-fido2-user-interface.service";
 import { DesktopSettingsService } from "../../platform/services/desktop-settings.service";
 
 @Component({
   standalone: true,
+  imports: [CommonModule],
   template: `
     <div
       style="background:white; display:flex; justify-content: center; align-items: center; flex-direction: column"
     >
       <h1 style="color: black">Select your passkey</h1>
+
+      <div *ngFor="let item of cipherIds$ | async">
+        <button
+          style="color:black; padding: 10px 20px; border: 1px solid blue; margin: 10px"
+          bitButton
+          type="button"
+          buttonType="secondary"
+          (click)="chooseCipher(item)"
+        >
+          {{ item }}
+        </button>
+      </div>
+
       <br />
+      <button
+        style="color:black; padding: 10px 20px; border: 1px solid black; margin: 10px"
+        bitButton
+        type="button"
+        buttonType="secondary"
+        (click)="confirmPasskey()"
+      >
+        Confirm passkey
+      </button>
       <button
         style="color:black; padding: 10px 20px; border: 1px solid black; margin: 10px"
         bitButton
@@ -23,14 +52,69 @@ import { DesktopSettingsService } from "../../platform/services/desktop-settings
     </div>
   `,
 })
-export class Fido2PlaceholderComponent {
+export class Fido2PlaceholderComponent implements OnInit, OnDestroy {
+  session?: DesktopFido2UserInterfaceSession = null;
+  private cipherIdsSubject = new BehaviorSubject<string[]>([]);
+  cipherIds$: Observable<string[]>;
+
   constructor(
     private readonly desktopSettingsService: DesktopSettingsService,
+    private readonly fido2UserInterfaceService: DesktopFido2UserInterfaceService,
     private readonly router: Router,
   ) {}
 
+  ngOnInit() {
+    this.session = this.fido2UserInterfaceService.getCurrentSession();
+    this.cipherIds$ = this.session?.availableCipherIds$;
+  }
+
+  async chooseCipher(cipherId: string) {
+    // For now: Set UV to true
+    this.session?.confirmChosenCipher(cipherId, true);
+
+    await this.router.navigate(["/"]);
+    await this.desktopSettingsService.setModalMode(false);
+  }
+
+  ngOnDestroy() {
+    this.cipherIdsSubject.complete(); // Clean up the BehaviorSubject
+  }
+
+  async confirmPasskey() {
+    try {
+      // Retrieve the current UI session to control the flow
+      if (!this.session) {
+        // todo: handle error
+        throw new Error("No session found");
+      }
+
+      // If we want to we could submit information to the session in order to create the credential
+      // const cipher = await session.createCredential({
+      //   userHandle: "userHandle2",
+      //   userName: "username2",
+      //   credentialName: "zxsd2",
+      //   rpId: "webauthn.io",
+      //   userVerification: true,
+      // });
+
+      this.session.notifyConfirmNewCredential(true);
+
+      // Not sure this clean up should happen here or in session.
+      // The session currently toggles modal on and send us here
+      // But if this route is somehow opened outside of session we want to make sure we clean up?
+      await this.router.navigate(["/"]);
+      await this.desktopSettingsService.setModalMode(false);
+    } catch {
+      // TODO: Handle error appropriately
+    }
+  }
+
   async closeModal() {
     await this.router.navigate(["/"]);
-    await this.desktopSettingsService.setInModalMode(false);
+    await this.desktopSettingsService.setModalMode(false);
+
+    this.session.notifyConfirmNewCredential(false);
+    // little bit hacky:
+    this.session.confirmChosenCipher(null);
   }
 }
diff --git a/apps/desktop/src/app/services/services.module.ts b/apps/desktop/src/app/services/services.module.ts
index 66e3175fee7..db28f01f27a 100644
--- a/apps/desktop/src/app/services/services.module.ts
+++ b/apps/desktop/src/app/services/services.module.ts
@@ -1,6 +1,7 @@
 // FIXME: Update this file to be type safe and remove this and next line
 // @ts-strict-ignore
 import { APP_INITIALIZER, NgModule } from "@angular/core";
+import { Router } from "@angular/router";
 import { Subject, merge } from "rxjs";
 
 import { OrganizationUserApiService } from "@bitwarden/admin-console/common";
@@ -334,9 +335,21 @@ const safeProviders: SafeProvider[] = [
     ],
   }),
   safeProvider({
-    provide: Fido2UserInterfaceServiceAbstraction,
+    provide: DesktopFido2UserInterfaceService,
     useClass: DesktopFido2UserInterfaceService,
-    deps: [AuthServiceAbstraction, CipherServiceAbstraction, AccountService, LogService],
+    deps: [
+      AuthServiceAbstraction,
+      CipherServiceAbstraction,
+      AccountService,
+      LogService,
+      MessagingServiceAbstraction,
+      Router,
+      DesktopSettingsService,
+    ],
+  }),
+  safeProvider({
+    provide: Fido2UserInterfaceServiceAbstraction, // We utilize desktop specific methods when wiring OS API's
+    useExisting: DesktopFido2UserInterfaceService,
   }),
   safeProvider({
     provide: Fido2AuthenticatorServiceAbstraction,
diff --git a/apps/desktop/src/autofill/preload.ts b/apps/desktop/src/autofill/preload.ts
index 494544f5858..2c006b5c928 100644
--- a/apps/desktop/src/autofill/preload.ts
+++ b/apps/desktop/src/autofill/preload.ts
@@ -80,6 +80,44 @@ export default {
             return;
           }
 
+          ipcRenderer.send("autofill.completePasskeyAssertion", {
+            clientId,
+            sequenceNumber,
+            response,
+          });
+        });
+      },
+    );
+  },
+  listenPasskeyAssertionWithoutUserInterface: (
+    fn: (
+      clientId: number,
+      sequenceNumber: number,
+      request: autofill.PasskeyAssertionWithoutUserInterfaceRequest,
+      completeCallback: (error: Error | null, response: autofill.PasskeyAssertionResponse) => void,
+    ) => void,
+  ) => {
+    ipcRenderer.on(
+      "autofill.passkeyAssertionWithoutUserInterface",
+      (
+        event,
+        data: {
+          clientId: number;
+          sequenceNumber: number;
+          request: autofill.PasskeyAssertionWithoutUserInterfaceRequest;
+        },
+      ) => {
+        const { clientId, sequenceNumber, request } = data;
+        fn(clientId, sequenceNumber, request, (error, response) => {
+          if (error) {
+            ipcRenderer.send("autofill.completeError", {
+              clientId,
+              sequenceNumber,
+              error: error.message,
+            });
+            return;
+          }
+
           ipcRenderer.send("autofill.completePasskeyAssertion", {
             clientId,
             sequenceNumber,
diff --git a/apps/desktop/src/autofill/services/desktop-autofill.service.ts b/apps/desktop/src/autofill/services/desktop-autofill.service.ts
index 2ed5a649997..e88e16c2ffc 100644
--- a/apps/desktop/src/autofill/services/desktop-autofill.service.ts
+++ b/apps/desktop/src/autofill/services/desktop-autofill.service.ts
@@ -1,7 +1,6 @@
 import { Injectable, OnDestroy } from "@angular/core";
 import { autofill } from "desktop_native/napi";
 import {
-  EMPTY,
   Subject,
   distinctUntilChanged,
   filter,
@@ -10,6 +9,7 @@ import {
   mergeMap,
   switchMap,
   takeUntil,
+  EMPTY,
 } from "rxjs";
 
 import { AccountService } from "@bitwarden/common/auth/abstractions/account.service";
@@ -26,9 +26,9 @@ import {
 } from "@bitwarden/common/platform/abstractions/fido2/fido2-authenticator.service.abstraction";
 import { LogService } from "@bitwarden/common/platform/abstractions/log.service";
 import { Utils } from "@bitwarden/common/platform/misc/utils";
+import { parseCredentialId } from "@bitwarden/common/platform/services/fido2/credential-id-utils";
 import { getCredentialsForAutofill } from "@bitwarden/common/platform/services/fido2/fido2-autofill-utils";
 import { Fido2Utils } from "@bitwarden/common/platform/services/fido2/fido2-utils";
-import { guidToRawFormat } from "@bitwarden/common/platform/services/fido2/guid-utils";
 import { UserId } from "@bitwarden/common/types/guid";
 import { CipherService } from "@bitwarden/common/vault/abstractions/cipher.service";
 import { CipherType } from "@bitwarden/common/vault/enums";
@@ -41,6 +41,8 @@ import {
   NativeAutofillSyncCommand,
 } from "../../platform/main/autofill/sync.command";
 
+import type { NativeWindowObject } from "./desktop-fido2-user-interface.service";
+
 @Injectable()
 export class DesktopAutofillService implements OnDestroy {
   private destroy$ = new Subject<void>();
@@ -49,7 +51,7 @@ export class DesktopAutofillService implements OnDestroy {
     private logService: LogService,
     private cipherService: CipherService,
     private configService: ConfigService,
-    private fido2AuthenticatorService: Fido2AuthenticatorServiceAbstraction<void>,
+    private fido2AuthenticatorService: Fido2AuthenticatorServiceAbstraction<NativeWindowObject>,
     private accountService: AccountService,
   ) {}
 
@@ -155,7 +157,11 @@ export class DesktopAutofillService implements OnDestroy {
 
       const controller = new AbortController();
       void this.fido2AuthenticatorService
-        .makeCredential(this.convertRegistrationRequest(request), null, controller)
+        .makeCredential(
+          this.convertRegistrationRequest(request),
+          { windowXy: request.windowXy },
+          controller,
+        )
         .then((response) => {
           callback(null, this.convertRegistrationResponse(request, response));
         })
@@ -165,47 +171,77 @@ export class DesktopAutofillService implements OnDestroy {
         });
     });
 
+    ipc.autofill.listenPasskeyAssertionWithoutUserInterface(
+      async (clientId, sequenceNumber, request, callback) => {
+        this.logService.warning(
+          "listenPasskeyAssertion without user interface",
+          clientId,
+          sequenceNumber,
+          request,
+        );
+
+        // For some reason the credentialId is passed as an empty array in the request, so we need to
+        // get it from the cipher. For that we use the recordIdentifier, which is the cipherId.
+        if (request.recordIdentifier && request.credentialId.length === 0) {
+          const activeUserId = await firstValueFrom(
+            this.accountService.activeAccount$.pipe(getOptionalUserId),
+          );
+          if (!activeUserId) {
+            this.logService.error("listenPasskeyAssertion error", "Active user not found");
+            callback(new Error("Active user not found"), null);
+            return;
+          }
+
+          const cipher = await this.cipherService.get(request.recordIdentifier, activeUserId);
+          if (!cipher) {
+            this.logService.error("listenPasskeyAssertion error", "Cipher not found");
+            callback(new Error("Cipher not found"), null);
+            return;
+          }
+
+          const decrypted = await cipher.decrypt(
+            await this.cipherService.getKeyForCipherKeyDecryption(cipher, activeUserId),
+          );
+
+          const fido2Credential = decrypted.login.fido2Credentials?.[0];
+          if (!fido2Credential) {
+            this.logService.error("listenPasskeyAssertion error", "Fido2Credential not found");
+            callback(new Error("Fido2Credential not found"), null);
+            return;
+          }
+
+          request.credentialId = Array.from(
+            parseCredentialId(decrypted.login.fido2Credentials?.[0].credentialId),
+          );
+        }
+
+        const controller = new AbortController();
+        void this.fido2AuthenticatorService
+          .getAssertion(
+            this.convertAssertionRequest(request),
+            { windowXy: request.windowXy },
+            controller,
+          )
+          .then((response) => {
+            callback(null, this.convertAssertionResponse(request, response));
+          })
+          .catch((error) => {
+            this.logService.error("listenPasskeyAssertion error", error);
+            callback(error, null);
+          });
+      },
+    );
+
     ipc.autofill.listenPasskeyAssertion(async (clientId, sequenceNumber, request, callback) => {
       this.logService.warning("listenPasskeyAssertion", clientId, sequenceNumber, request);
 
-      // TODO: For some reason the credentialId is passed as an empty array in the request, so we need to
-      // get it from the cipher. For that we use the recordIdentifier, which is the cipherId.
-      if (request.recordIdentifier && request.credentialId.length === 0) {
-        const activeUserId = await firstValueFrom(
-          this.accountService.activeAccount$.pipe(getOptionalUserId),
-        );
-        if (!activeUserId) {
-          this.logService.error("listenPasskeyAssertion error", "Active user not found");
-          callback(new Error("Active user not found"), null);
-          return;
-        }
-
-        const cipher = await this.cipherService.get(request.recordIdentifier, activeUserId);
-        if (!cipher) {
-          this.logService.error("listenPasskeyAssertion error", "Cipher not found");
-          callback(new Error("Cipher not found"), null);
-          return;
-        }
-
-        const decrypted = await cipher.decrypt(
-          await this.cipherService.getKeyForCipherKeyDecryption(cipher, activeUserId),
-        );
-
-        const fido2Credential = decrypted.login.fido2Credentials?.[0];
-        if (!fido2Credential) {
-          this.logService.error("listenPasskeyAssertion error", "Fido2Credential not found");
-          callback(new Error("Fido2Credential not found"), null);
-          return;
-        }
-
-        request.credentialId = Array.from(
-          guidToRawFormat(decrypted.login.fido2Credentials?.[0].credentialId),
-        );
-      }
-
       const controller = new AbortController();
       void this.fido2AuthenticatorService
-        .getAssertion(this.convertAssertionRequest(request), null, controller)
+        .getAssertion(
+          this.convertAssertionRequest(request),
+          { windowXy: request.windowXy },
+          controller,
+        )
         .then((response) => {
           callback(null, this.convertAssertionResponse(request, response));
         })
@@ -257,27 +293,48 @@ export class DesktopAutofillService implements OnDestroy {
     };
   }
 
+  /**
+   *
+   * @param request
+   * @param assumeUserPresence For WithoutUserInterface requests, we assume the user is present
+   * @returns
+   */
   private convertAssertionRequest(
-    request: autofill.PasskeyAssertionRequest,
+    request:
+      | autofill.PasskeyAssertionRequest
+      | autofill.PasskeyAssertionWithoutUserInterfaceRequest,
   ): Fido2AuthenticatorGetAssertionParams {
+    let allowedCredentials;
+    if ("credentialId" in request) {
+      allowedCredentials = [
+        {
+          id: new Uint8Array(request.credentialId),
+          type: "public-key" as const,
+        },
+      ];
+    } else {
+      allowedCredentials = request.allowedCredentials.map((credentialId) => ({
+        id: new Uint8Array(credentialId),
+        type: "public-key" as const,
+      }));
+    }
+
     return {
       rpId: request.rpId,
       hash: new Uint8Array(request.clientDataHash),
-      allowCredentialDescriptorList: [
-        {
-          id: new Uint8Array(request.credentialId),
-          type: "public-key",
-        },
-      ],
+      allowCredentialDescriptorList: allowedCredentials,
       extensions: {},
       requireUserVerification:
         request.userVerification === "required" || request.userVerification === "preferred",
       fallbackSupported: false,
+      assumeUserPresence: true, // For desktop assertions, it's safe to assume UP has been checked by OS dialogues
     };
   }
 
   private convertAssertionResponse(
-    request: autofill.PasskeyAssertionRequest,
+    request:
+      | autofill.PasskeyAssertionRequest
+      | autofill.PasskeyAssertionWithoutUserInterfaceRequest,
     response: Fido2AuthenticatorGetAssertionResult,
   ): autofill.PasskeyAssertionResponse {
     return {
diff --git a/apps/desktop/src/autofill/services/desktop-fido2-user-interface.service.ts b/apps/desktop/src/autofill/services/desktop-fido2-user-interface.service.ts
index 684b19e7394..3caf13fa5b7 100644
--- a/apps/desktop/src/autofill/services/desktop-fido2-user-interface.service.ts
+++ b/apps/desktop/src/autofill/services/desktop-fido2-user-interface.service.ts
@@ -1,4 +1,14 @@
-import { firstValueFrom, map } from "rxjs";
+import { Router } from "@angular/router";
+import {
+  lastValueFrom,
+  firstValueFrom,
+  map,
+  Subject,
+  filter,
+  take,
+  BehaviorSubject,
+  timeout,
+} from "rxjs";
 
 import { AccountService } from "@bitwarden/common/auth/abstractions/account.service";
 import { AuthService } from "@bitwarden/common/auth/abstractions/auth.service";
@@ -10,8 +20,10 @@ import {
   PickCredentialParams,
 } from "@bitwarden/common/platform/abstractions/fido2/fido2-user-interface.service.abstraction";
 import { LogService } from "@bitwarden/common/platform/abstractions/log.service";
+import { MessagingService } from "@bitwarden/common/platform/abstractions/messaging.service";
 import { CipherService } from "@bitwarden/common/vault/abstractions/cipher.service";
 import { CipherRepromptType, CipherType, SecureNoteType } from "@bitwarden/common/vault/enums";
+import { Cipher } from "@bitwarden/common/vault/models/domain/cipher";
 import { CardView } from "@bitwarden/common/vault/models/view/card.view";
 import { CipherView } from "@bitwarden/common/vault/models/view/cipher.view";
 import { IdentityView } from "@bitwarden/common/vault/models/view/identity.view";
@@ -19,28 +31,54 @@ import { LoginUriView } from "@bitwarden/common/vault/models/view/login-uri.view
 import { LoginView } from "@bitwarden/common/vault/models/view/login.view";
 import { SecureNoteView } from "@bitwarden/common/vault/models/view/secure-note.view";
 
+import { DesktopSettingsService } from "../../platform/services/desktop-settings.service";
+
+/**
+ * This type is used to pass the window position from the native UI
+ */
+export type NativeWindowObject = {
+  /**
+   * The position of the window, first entry is the x position, second is the y position
+   */
+  windowXy?: { x: number; y: number };
+};
+
 export class DesktopFido2UserInterfaceService
-  implements Fido2UserInterfaceServiceAbstraction<void>
+  implements Fido2UserInterfaceServiceAbstraction<NativeWindowObject>
 {
   constructor(
     private authService: AuthService,
     private cipherService: CipherService,
     private accountService: AccountService,
     private logService: LogService,
+    private messagingService: MessagingService,
+    private router: Router,
+    private desktopSettingsService: DesktopSettingsService,
   ) {}
+  private currentSession: any;
+
+  getCurrentSession(): DesktopFido2UserInterfaceSession | undefined {
+    return this.currentSession;
+  }
 
   async newSession(
     fallbackSupported: boolean,
-    _tab: void,
+    nativeWindowObject: NativeWindowObject,
     abortController?: AbortController,
   ): Promise<DesktopFido2UserInterfaceSession> {
-    this.logService.warning("newSession", fallbackSupported, abortController);
-    return new DesktopFido2UserInterfaceSession(
+    this.logService.warning("newSession", fallbackSupported, abortController, nativeWindowObject);
+    const session = new DesktopFido2UserInterfaceSession(
       this.authService,
       this.cipherService,
       this.accountService,
       this.logService,
+      this.router,
+      this.desktopSettingsService,
+      nativeWindowObject,
     );
+
+    this.currentSession = session;
+    return session;
   }
 }
 
@@ -50,17 +88,110 @@ export class DesktopFido2UserInterfaceSession implements Fido2UserInterfaceSessi
     private cipherService: CipherService,
     private accountService: AccountService,
     private logService: LogService,
+    private router: Router,
+    private desktopSettingsService: DesktopSettingsService,
+    private windowObject: NativeWindowObject,
   ) {}
 
+  private confirmCredentialSubject = new Subject<boolean>();
+  private createdCipher: Cipher;
+
+  private availableCipherIdsSubject = new BehaviorSubject<string[]>(null);
+  /**
+   * Observable that emits available cipher IDs once they're confirmed by the UI
+   */
+  availableCipherIds$ = this.availableCipherIdsSubject.pipe(
+    filter((ids) => ids != null),
+    take(1),
+  );
+
+  private chosenCipherSubject = new Subject<{ cipherId: string; userVerified: boolean }>();
+
+  // Method implementation
   async pickCredential({
     cipherIds,
     userVerification,
+    assumeUserPresence,
+    masterPasswordRepromptRequired,
   }: PickCredentialParams): Promise<{ cipherId: string; userVerified: boolean }> {
-    this.logService.warning("pickCredential", cipherIds, userVerification);
+    this.logService.warning("pickCredential desktop function", {
+      cipherIds,
+      userVerification,
+      assumeUserPresence,
+      masterPasswordRepromptRequired,
+    });
 
-    return { cipherId: cipherIds[0], userVerified: userVerification };
+    try {
+      // Check if we can return the credential without user interaction
+      if (assumeUserPresence && cipherIds.length === 1 && !masterPasswordRepromptRequired) {
+        this.logService.debug(
+          "shortcut - Assuming user presence and returning cipherId",
+          cipherIds[0],
+        );
+        return { cipherId: cipherIds[0], userVerified: userVerification };
+      }
+
+      this.logService.debug("Could not shortcut, showing UI");
+
+      // make the cipherIds available to the UI.
+      this.availableCipherIdsSubject.next(cipherIds);
+
+      await this.showUi("/passkeys", this.windowObject.windowXy);
+
+      const chosenCipherResponse = await this.waitForUiChosenCipher();
+
+      this.logService.debug("Received chosen cipher", chosenCipherResponse);
+
+      return {
+        cipherId: chosenCipherResponse.cipherId,
+        userVerified: chosenCipherResponse.userVerified,
+      };
+    } finally {
+      // Make sure to clean up so the app is never stuck in modal mode?
+      await this.desktopSettingsService.setModalMode(false);
+    }
   }
 
+  confirmChosenCipher(cipherId: string, userVerified: boolean = false): void {
+    this.chosenCipherSubject.next({ cipherId, userVerified });
+    this.chosenCipherSubject.complete();
+  }
+
+  private async waitForUiChosenCipher(
+    timeoutMs: number = 60000,
+  ): Promise<{ cipherId: string; userVerified: boolean } | undefined> {
+    try {
+      return await lastValueFrom(this.chosenCipherSubject.pipe(timeout(timeoutMs)));
+    } catch {
+      // If we hit a timeout, return undefined instead of throwing
+      this.logService.warning("Timeout: User did not select a cipher within the allowed time", {
+        timeoutMs,
+      });
+      return { cipherId: undefined, userVerified: false };
+    }
+  }
+
+  /**
+   * Notifies the Fido2UserInterfaceSession that the UI operations has completed and it can return to the OS.
+   */
+  notifyConfirmNewCredential(confirmed: boolean): void {
+    this.confirmCredentialSubject.next(confirmed);
+    this.confirmCredentialSubject.complete();
+  }
+
+  /**
+   * Returns once the UI has confirmed and completed the operation
+   * @returns
+   */
+  private async waitForUiNewCredentialConfirmation(): Promise<boolean> {
+    return lastValueFrom(this.confirmCredentialSubject);
+  }
+
+  /**
+   * This is called by the OS. It loads the UI and waits for the user to confirm the new credential. Once the UI has confirmed, it returns to the the OS.
+   * @param param0
+   * @returns
+   */
   async confirmNewCredential({
     credentialName,
     userName,
@@ -75,6 +206,48 @@ export class DesktopFido2UserInterfaceSession implements Fido2UserInterfaceSessi
       rpId,
     );
 
+    try {
+      await this.showUi("/passkeys", this.windowObject.windowXy);
+
+      // Wait for the UI to wrap up
+      const confirmation = await this.waitForUiNewCredentialConfirmation();
+      if (!confirmation) {
+        return { cipherId: undefined, userVerified: false };
+      }
+      // Create the credential
+      await this.createCredential({
+        credentialName,
+        userName,
+        rpId,
+        userHandle: "",
+        userVerification,
+      });
+
+      // wait for 10ms to help RXJS catch up(?)
+      // We sometimes get a race condition from this.createCredential not updating cipherService in time
+      //console.log("waiting 10ms..");
+      //await new Promise((resolve) => setTimeout(resolve, 10));
+      //console.log("Just waited 10ms");
+
+      // Return the new cipher (this.createdCipher)
+      return { cipherId: this.createdCipher.id, userVerified: userVerification };
+    } finally {
+      // Make sure to clean up so the app is never stuck in modal mode?
+      await this.desktopSettingsService.setModalMode(false);
+    }
+  }
+
+  private async showUi(route: string, position?: { x: number; y: number }): Promise<void> {
+    // Load the UI:
+    await this.desktopSettingsService.setModalMode(true, position);
+    await this.router.navigate(["/passkeys"]);
+  }
+
+  /**
+   * Can be called by the UI to create a new credential with user input etc.
+   * @param param0
+   */
+  async createCredential({ credentialName, userName, rpId }: NewCredentialParams): Promise<Cipher> {
     // Store the passkey on a new cipher to avoid replacing something important
     const cipher = new CipherView();
     cipher.name = credentialName;
@@ -97,7 +270,9 @@ export class DesktopFido2UserInterfaceSession implements Fido2UserInterfaceSessi
     const encCipher = await this.cipherService.encrypt(cipher, activeUserId);
     const createdCipher = await this.cipherService.createWithServer(encCipher);
 
-    return { cipherId: createdCipher.id, userVerified: userVerification };
+    this.createdCipher = createdCipher;
+
+    return createdCipher;
   }
 
   async informExcludedCredential(existingCipherIds: string[]): Promise<void> {
diff --git a/apps/desktop/src/main.ts b/apps/desktop/src/main.ts
index e4894b159fe..20c632ec4ac 100644
--- a/apps/desktop/src/main.ts
+++ b/apps/desktop/src/main.ts
@@ -209,6 +209,14 @@ export class Main {
       new ElectronMainMessagingService(this.windowMain),
     );
 
+    this.trayMain = new TrayMain(
+      this.windowMain,
+      this.i18nService,
+      this.desktopSettingsService,
+      this.messagingService,
+      this.biometricsService,
+    );
+
     messageSubject.asObservable().subscribe((message) => {
       void this.messagingMain.onMessage(message).catch((err) => {
         this.logService.error(
@@ -236,7 +244,7 @@ export class Main {
       this.windowMain,
       this.i18nService,
       this.desktopSettingsService,
-      biometricStateService,
+      this.messagingService,
       this.biometricsService,
     );
 
@@ -285,7 +293,7 @@ export class Main {
       async () => {
         await this.toggleHardwareAcceleration();
         // Reset modal mode to make sure main window is displayed correctly
-        await this.desktopSettingsService.resetInModalMode();
+        await this.desktopSettingsService.resetModalMode();
         await this.windowMain.init();
         await this.i18nService.init();
         await this.messagingMain.init();
diff --git a/apps/desktop/src/main/messaging.main.ts b/apps/desktop/src/main/messaging.main.ts
index 0d86a7234e6..bb4063d64fd 100644
--- a/apps/desktop/src/main/messaging.main.ts
+++ b/apps/desktop/src/main/messaging.main.ts
@@ -37,6 +37,10 @@ export class MessagingMain {
 
   async onMessage(message: any) {
     switch (message.command) {
+      case "loadurl":
+        // TODO: Remove this once fakepopup is removed from tray (just used for dev)
+        await this.main.windowMain.loadUrl(message.url, message.modal);
+        break;
       case "scheduleNextSync":
         this.scheduleNextSync();
         break;
diff --git a/apps/desktop/src/main/tray.main.ts b/apps/desktop/src/main/tray.main.ts
index e63e2a00c85..b7ddefe6e1b 100644
--- a/apps/desktop/src/main/tray.main.ts
+++ b/apps/desktop/src/main/tray.main.ts
@@ -1,16 +1,16 @@
 // FIXME: Update this file to be type safe and remove this and next line
 // @ts-strict-ignore
 import * as path from "path";
-import * as url from "url";
 
 import { app, BrowserWindow, Menu, MenuItemConstructorOptions, nativeImage, Tray } from "electron";
 import { firstValueFrom } from "rxjs";
 
 import { I18nService } from "@bitwarden/common/platform/abstractions/i18n.service";
-import { BiometricStateService, BiometricsService } from "@bitwarden/key-management";
+import { MessagingService } from "@bitwarden/common/platform/abstractions/messaging.service";
+import { BiometricsService } from "@bitwarden/key-management";
 
 import { DesktopSettingsService } from "../platform/services/desktop-settings.service";
-import { cleanUserAgent, isDev } from "../utils";
+import { isDev } from "../utils";
 
 import { WindowMain } from "./window.main";
 
@@ -26,7 +26,7 @@ export class TrayMain {
     private windowMain: WindowMain,
     private i18nService: I18nService,
     private desktopSettingsService: DesktopSettingsService,
-    private biometricsStateService: BiometricStateService,
+    private messagingService: MessagingService,
     private biometricService: BiometricsService,
   ) {
     if (process.platform === "win32") {
@@ -216,32 +216,6 @@ export class TrayMain {
    * @returns
    */
   private async fakePopup() {
-    if (this.windowMain.win == null || this.windowMain.win.isDestroyed()) {
-      await this.windowMain.createWindow("modal-app");
-      return;
-    }
-
-    // Restyle existing
-    const existingWin = this.windowMain.win;
-
-    await this.desktopSettingsService.setInModalMode(true);
-    await existingWin.loadURL(
-      url.format({
-        protocol: "file:",
-        //pathname: `${__dirname}/index.html`,
-        pathname: path.join(__dirname, "/index.html"),
-        slashes: true,
-        hash: "/passkeys",
-        query: {
-          redirectUrl: "/passkeys",
-        },
-      }),
-      {
-        userAgent: cleanUserAgent(existingWin.webContents.userAgent),
-      },
-    );
-    existingWin.once("ready-to-show", () => {
-      existingWin.show();
-    });
+    await this.messagingService.send("loadurl", { url: "/passkeys", modal: true });
   }
 }
diff --git a/apps/desktop/src/main/window.main.ts b/apps/desktop/src/main/window.main.ts
index ca154400ff5..73231f1f730 100644
--- a/apps/desktop/src/main/window.main.ts
+++ b/apps/desktop/src/main/window.main.ts
@@ -78,18 +78,19 @@ export class WindowMain {
       }
     });
 
-    this.desktopSettingsService.inModalMode$
+    this.desktopSettingsService.modalMode$
       .pipe(
         pairwise(),
         concatMap(async ([lastValue, newValue]) => {
-          if (lastValue && !newValue) {
+          if (lastValue.isModalModeActive && !newValue.isModalModeActive) {
             // Reset the window state to the main window state
             applyMainWindowStyles(this.win, this.windowStates[mainWindowSizeKey]);
             // Because modal is used in front of another app, UX wise it makes sense to hide the main window when leaving modal mode.
             this.win.hide();
-          } else if (!lastValue && newValue) {
+          } else if (!lastValue.isModalModeActive && newValue.isModalModeActive) {
             // Apply the popup modal styles
-            applyPopupModalStyles(this.win);
+            this.logService.info("Applying popup modal styles", newValue.modalPosition);
+            applyPopupModalStyles(this.win, newValue.modalPosition);
             this.win.show();
           }
         }),
@@ -209,6 +210,35 @@ export class WindowMain {
     }
   }
 
+  // TODO: REMOVE ONCE WE CAN STOP USING FAKE POP UP BTN FROM TRAY
+  // Only used for development
+  async loadUrl(targetPath: string, modal: boolean = false) {
+    if (this.win == null || this.win.isDestroyed()) {
+      await this.createWindow("modal-app");
+      return;
+    }
+
+    await this.desktopSettingsService.setModalMode(modal);
+    await this.win.loadURL(
+      url.format({
+        protocol: "file:",
+        //pathname: `${__dirname}/index.html`,
+        pathname: path.join(__dirname, "/index.html"),
+        slashes: true,
+        hash: targetPath,
+        query: {
+          redirectUrl: targetPath,
+        },
+      }),
+      {
+        userAgent: cleanUserAgent(this.win.webContents.userAgent),
+      },
+    );
+    this.win.once("ready-to-show", () => {
+      this.win.show();
+    });
+  }
+
   /**
    * Creates the main window. The template argument is used to determine the styling of the window and what url will be loaded.
    * When the template is "modal-app", the window will be styled as a modal and the passkeys page will be loaded.
@@ -394,9 +424,9 @@ export class WindowMain {
       return;
     }
 
-    const inModalMode = await firstValueFrom(this.desktopSettingsService.inModalMode$);
+    const modalMode = await firstValueFrom(this.desktopSettingsService.modalMode$);
 
-    if (inModalMode) {
+    if (modalMode.isModalModeActive) {
       return;
     }
 
diff --git a/apps/desktop/src/platform/main/autofill/native-autofill.main.ts b/apps/desktop/src/platform/main/autofill/native-autofill.main.ts
index 1465831340f..f66eea180cf 100644
--- a/apps/desktop/src/platform/main/autofill/native-autofill.main.ts
+++ b/apps/desktop/src/platform/main/autofill/native-autofill.main.ts
@@ -40,6 +40,7 @@ export class NativeAutofillMain {
       (error, clientId, sequenceNumber, request) => {
         if (error) {
           this.logService.error("autofill.IpcServer.registration", error);
+          this.ipcServer.completeError(clientId, sequenceNumber, String(error));
           return;
         }
         this.windowMain.win.webContents.send("autofill.passkeyRegistration", {
@@ -52,6 +53,7 @@ export class NativeAutofillMain {
       (error, clientId, sequenceNumber, request) => {
         if (error) {
           this.logService.error("autofill.IpcServer.assertion", error);
+          this.ipcServer.completeError(clientId, sequenceNumber, String(error));
           return;
         }
         this.windowMain.win.webContents.send("autofill.passkeyAssertion", {
@@ -60,6 +62,19 @@ export class NativeAutofillMain {
           request,
         });
       },
+      // AssertionWithoutUserInterfaceCallback
+      (error, clientId, sequenceNumber, request) => {
+        if (error) {
+          this.logService.error("autofill.IpcServer.assertion", error);
+          this.ipcServer.completeError(clientId, sequenceNumber, String(error));
+          return;
+        }
+        this.windowMain.win.webContents.send("autofill.passkeyAssertionWithoutUserInterface", {
+          clientId,
+          sequenceNumber,
+          request,
+        });
+      },
     );
 
     ipcMain.on("autofill.completePasskeyRegistration", (event, data) => {
@@ -77,7 +92,7 @@ export class NativeAutofillMain {
     ipcMain.on("autofill.completeError", (event, data) => {
       this.logService.warning("autofill.completeError", data);
       const { clientId, sequenceNumber, error } = data;
-      this.ipcServer.completeAssertion(clientId, sequenceNumber, error);
+      this.ipcServer.completeError(clientId, sequenceNumber, String(error));
     });
   }
 
diff --git a/apps/desktop/src/platform/models/domain/window-state.ts b/apps/desktop/src/platform/models/domain/window-state.ts
index 00230319972..0efc9a1efab 100644
--- a/apps/desktop/src/platform/models/domain/window-state.ts
+++ b/apps/desktop/src/platform/models/domain/window-state.ts
@@ -11,3 +11,8 @@ export class WindowState {
   y?: number;
   zoomFactor?: number;
 }
+
+export class ModalModeState {
+  isModalModeActive: boolean;
+  modalPosition?: { x: number; y: number }; // Modal position is often passed from the native UI
+}
diff --git a/apps/desktop/src/platform/popup-modal-styles.ts b/apps/desktop/src/platform/popup-modal-styles.ts
index 9c3f06b34bf..ae46ebb5c76 100644
--- a/apps/desktop/src/platform/popup-modal-styles.ts
+++ b/apps/desktop/src/platform/popup-modal-styles.ts
@@ -6,10 +6,11 @@ import { WindowState } from "./models/domain/window-state";
 const popupWidth = 680;
 const popupHeight = 500;
 
-export function applyPopupModalStyles(window: BrowserWindow) {
+type Position = { x: number; y: number };
+
+export function applyPopupModalStyles(window: BrowserWindow, position?: Position) {
   window.unmaximize();
   window.setSize(popupWidth, popupHeight);
-  window.center();
   window.setWindowButtonVisibility?.(false);
   window.setMenuBarVisibility?.(false);
   window.setResizable(false);
@@ -20,8 +21,21 @@ export function applyPopupModalStyles(window: BrowserWindow) {
     window.setFullScreen(false);
     window.once("leave-full-screen", () => {
       window.setSize(popupWidth, popupHeight);
-      window.center();
+      positionWindow(window, position);
     });
+  } else {
+    // If not in full screen
+    positionWindow(window, position);
+  }
+}
+
+function positionWindow(window: BrowserWindow, position?: Position) {
+  if (position) {
+    const centeredX = position.x - popupWidth / 2;
+    const centeredY = position.y - popupHeight / 2;
+    window.setPosition(centeredX, centeredY);
+  } else {
+    window.center();
   }
 }
 
diff --git a/apps/desktop/src/platform/services/desktop-settings.service.ts b/apps/desktop/src/platform/services/desktop-settings.service.ts
index efac0cda252..f5789d6f40c 100644
--- a/apps/desktop/src/platform/services/desktop-settings.service.ts
+++ b/apps/desktop/src/platform/services/desktop-settings.service.ts
@@ -8,7 +8,7 @@ import {
 } from "@bitwarden/common/platform/state";
 import { UserId } from "@bitwarden/common/types/guid";
 
-import { WindowState } from "../models/domain/window-state";
+import { ModalModeState, WindowState } from "../models/domain/window-state";
 
 export const HARDWARE_ACCELERATION = new KeyDefinition<boolean>(
   DESKTOP_SETTINGS_DISK,
@@ -75,7 +75,7 @@ const MINIMIZE_ON_COPY = new UserKeyDefinition<boolean>(DESKTOP_SETTINGS_DISK, "
   clearOn: [], // User setting, no need to clear
 });
 
-const IN_MODAL_MODE = new KeyDefinition<boolean>(DESKTOP_SETTINGS_DISK, "inModalMode", {
+const MODAL_MODE = new KeyDefinition<ModalModeState>(DESKTOP_SETTINGS_DISK, "modalMode", {
   deserializer: (b) => b,
 });
 
@@ -174,9 +174,9 @@ export class DesktopSettingsService {
    */
   minimizeOnCopy$ = this.minimizeOnCopyState.state$.pipe(map(Boolean));
 
-  private readonly inModalModeState = this.stateProvider.getGlobal(IN_MODAL_MODE);
+  private readonly modalModeState = this.stateProvider.getGlobal(MODAL_MODE);
 
-  inModalMode$ = this.inModalModeState.state$.pipe(map(Boolean));
+  modalMode$ = this.modalModeState.state$;
 
   constructor(private stateProvider: StateProvider) {
     this.window$ = this.windowState.state$.pipe(
@@ -190,8 +190,8 @@ export class DesktopSettingsService {
    * This is used to clear the setting on application start to make sure we don't end up
    * stuck in modal mode if the application is force-closed in modal mode.
    */
-  async resetInModalMode() {
-    await this.inModalModeState.update(() => false);
+  async resetModalMode() {
+    await this.modalModeState.update(() => ({ isModalModeActive: false }));
   }
 
   async setHardwareAcceleration(enabled: boolean) {
@@ -306,8 +306,11 @@ export class DesktopSettingsService {
    * Sets the modal mode of the application. Setting this changes the windows-size and other properties.
    * @param value `true` if the application is in modal mode, `false` if it is not.
    */
-  async setInModalMode(value: boolean) {
-    await this.inModalModeState.update(() => value);
+  async setModalMode(value: boolean, modalPosition?: { x: number; y: number }) {
+    await this.modalModeState.update(() => ({
+      isModalModeActive: value,
+      modalPosition,
+    }));
   }
 
   /**
diff --git a/libs/common/src/platform/abstractions/fido2/fido2-user-interface.service.abstraction.ts b/libs/common/src/platform/abstractions/fido2/fido2-user-interface.service.abstraction.ts
index 7beefc3b4cc..1f871f6c70f 100644
--- a/libs/common/src/platform/abstractions/fido2/fido2-user-interface.service.abstraction.ts
+++ b/libs/common/src/platform/abstractions/fido2/fido2-user-interface.service.abstraction.ts
@@ -82,7 +82,7 @@ export abstract class Fido2UserInterfaceSession {
    *
    * @param params The parameters to use when asking the user to pick a credential.
    * @param abortController An abort controller that can be used to cancel/close the session.
-   * @returns The ID of the cipher that contains the credentials the user picked.
+   * @returns The ID of the cipher that contains the credentials the user picked. If not cipher was picked, return cipherId = undefined to to let the authenticator throw the error.
    */
   pickCredential: (
     params: PickCredentialParams,