diff --git a/zerver/views/sentry.py b/zerver/views/sentry.py
index 0a66c683b6..a0c5b31cab 100644
--- a/zerver/views/sentry.py
+++ b/zerver/views/sentry.py
@@ -1,5 +1,7 @@
 import urllib
+from contextlib import suppress
 
+import orjson
 from django.conf import settings
 from django.http import HttpRequest, HttpResponse
 from django.utils.translation import gettext as _
@@ -23,9 +25,9 @@ def sentry_tunnel(
     request: HttpRequest,
 ) -> HttpResponse:
     try:
-        envelope = request.body
-        header = to_wild_value("envelope", envelope.split(b"\n")[0].decode("utf-8"))
-        dsn = urllib.parse.urlparse(header["dsn"].tame(check_url))
+        envelope_header_line, envelope_items = request.body.split(b"\n", 1)
+        envelope_header = to_wild_value("envelope_header", envelope_header_line.decode("utf-8"))
+        dsn = urllib.parse.urlparse(envelope_header["dsn"].tame(check_url))
     except Exception:
         raise JsonableError(_("Invalid request format"))
 
@@ -35,7 +37,47 @@ def sentry_tunnel(
     assert dsn.hostname
     project_id = dsn.path.strip("/")
     url = dsn._replace(netloc=dsn.hostname, path=f"/api/{project_id}/envelope/").geturl()
+
+    # Adjust the payload to explicitly contain the IP address of the
+    # user we see.  If left blank, Sentry will assume the IP it
+    # received the request from, which is Zulip's, which can make
+    # debugging more complicated.
+    updated_body = request.body
+    # If we fail to update the body for any reason, leave it as-is; it
+    # is better to mis-report the IP than to drop the report entirely.
+    with suppress(Exception):
+        # This parses the Sentry ingestion format, known as an
+        # Envelope.  See https://develop.sentry.dev/sdk/envelopes/ for
+        # spec.
+        parts = [envelope_header_line, b"\n"]
+        while envelope_items != b"":
+            item_header_line, rest = envelope_items.split(b"\n", 1)
+            parts.append(item_header_line)
+            parts.append(b"\n")
+            item_header = orjson.loads(item_header_line.decode("utf-8"))
+            length = item_header.get("length")
+            if length is None:
+                item_body, envelope_items = ([*rest.split(b"\n", 1), b""])[:2]
+            else:
+                item_body, envelope_items = rest[0:length], rest[length:]
+            if item_header.get("type") in ("transaction", "event"):
+                # Event schema:
+                # https://develop.sentry.dev/sdk/event-payloads/#core-interfaces
+                # https://develop.sentry.dev/sdk/event-payloads/user/
+                #
+                # Transaction schema:
+                # https://develop.sentry.dev/sdk/event-payloads/transaction/#anatomy
+                # Note that "Transactions are Events enriched with Span data."
+                payload_data = orjson.loads(item_body)
+                if "user" in payload_data:
+                    payload_data["user"]["ip_address"] = request.META.get("REMOTE_ADDR")
+                    item_body = orjson.dumps(payload_data)
+            parts.append(item_body)
+            if length is None:
+                parts.append(b"\n")
+        updated_body = b"".join(parts)
+
     SentryTunnelSession().post(
-        url=url, data=envelope, headers={"Content-Type": "application/x-sentry-envelope"}
+        url=url, data=updated_body, headers={"Content-Type": "application/x-sentry-envelope"}
     ).raise_for_status()
     return HttpResponse(status=200)