diff --git a/db/migrate/20260525093000_change_captain_document_external_link_to_text.rb b/db/migrate/20260525093000_change_captain_document_external_link_to_text.rb
new file mode 100644
index 00000000000..50cee2b0df9
--- /dev/null
+++ b/db/migrate/20260525093000_change_captain_document_external_link_to_text.rb
@@ -0,0 +1,16 @@
+class ChangeCaptainDocumentExternalLinkToText < ActiveRecord::Migration[7.0]
+  OLD_INDEX_NAME = 'index_captain_documents_on_assistant_id_and_external_link'.freeze
+  NEW_INDEX_NAME = 'idx_captain_documents_on_assistant_id_and_external_link_md5'.freeze
+
+  def up
+    remove_index :captain_documents, name: OLD_INDEX_NAME, if_exists: true
+    change_column :captain_documents, :external_link, :text, null: false
+    add_index :captain_documents, 'assistant_id, md5(external_link)', unique: true, name: NEW_INDEX_NAME, if_not_exists: true
+  end
+
+  def down
+    remove_index :captain_documents, name: NEW_INDEX_NAME, if_exists: true
+    change_column :captain_documents, :external_link, :string, null: false
+    add_index :captain_documents, [:assistant_id, :external_link], unique: true, name: OLD_INDEX_NAME, if_not_exists: true
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index 9d9fe3cbc95..f2c47957137 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -10,7 +10,7 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema[7.1].define(version: 2026_05_15_000000) do
+ActiveRecord::Schema[7.1].define(version: 2026_05_25_093000) do
   # These extensions should be enabled to support this database
   enable_extension "pg_stat_statements"
   enable_extension "pg_trgm"
@@ -370,7 +370,7 @@ ActiveRecord::Schema[7.1].define(version: 2026_05_15_000000) do
 
   create_table "captain_documents", force: :cascade do |t|
     t.string "name"
-    t.string "external_link", null: false
+    t.text "external_link", null: false
     t.text "content"
     t.bigint "assistant_id", null: false
     t.bigint "account_id", null: false
@@ -381,10 +381,10 @@ ActiveRecord::Schema[7.1].define(version: 2026_05_15_000000) do
     t.integer "sync_status"
     t.datetime "last_synced_at"
     t.datetime "last_sync_attempted_at"
+    t.index "assistant_id, md5(external_link)", name: "idx_captain_documents_on_assistant_id_and_external_link_md5", unique: true
     t.index ["account_id", "assistant_id", "sync_status", "last_synced_at"], name: "idx_captain_documents_on_account_assistant_sync_stats"
     t.index ["account_id", "sync_status"], name: "index_captain_documents_on_account_id_and_sync_status"
     t.index ["account_id"], name: "index_captain_documents_on_account_id"
-    t.index ["assistant_id", "external_link"], name: "index_captain_documents_on_assistant_id_and_external_link", unique: true
     t.index ["assistant_id"], name: "index_captain_documents_on_assistant_id"
     t.index ["status"], name: "index_captain_documents_on_status"
   end
diff --git a/enterprise/app/models/captain/document.rb b/enterprise/app/models/captain/document.rb
index 0fe14813bd4..6eda0eb5ae2 100644
--- a/enterprise/app/models/captain/document.rb
+++ b/enterprise/app/models/captain/document.rb
@@ -5,7 +5,7 @@
 #  id                     :bigint           not null, primary key
 #  content                :text
 #  content_fingerprint    :string
-#  external_link          :string           not null
+#  external_link          :text             not null
 #  last_sync_attempted_at :datetime
 #  last_sync_error_code   :string
 #  last_synced_at         :datetime
@@ -20,12 +20,12 @@
 #
 # Indexes
 #
-#  idx_captain_documents_on_account_assistant_sync_stats      (account_id,assistant_id,sync_status,last_synced_at)
-#  index_captain_documents_on_account_id                      (account_id)
-#  index_captain_documents_on_account_id_and_sync_status      (account_id,sync_status)
-#  index_captain_documents_on_assistant_id                    (assistant_id)
-#  index_captain_documents_on_assistant_id_and_external_link  (assistant_id,external_link) UNIQUE
-#  index_captain_documents_on_status                          (status)
+#  idx_captain_documents_on_account_assistant_sync_stats        (account_id,assistant_id,sync_status,last_synced_at)
+#  idx_captain_documents_on_assistant_id_and_external_link_md5  (assistant_id, md5(external_link)) UNIQUE
+#  index_captain_documents_on_account_id                        (account_id)
+#  index_captain_documents_on_account_id_and_sync_status        (account_id,sync_status)
+#  index_captain_documents_on_assistant_id                      (assistant_id)
+#  index_captain_documents_on_status                            (status)
 #
 class Captain::Document < ApplicationRecord
   class LimitExceededError < StandardError; end
diff --git a/spec/enterprise/jobs/captain/tools/firecrawl_parser_job_spec.rb b/spec/enterprise/jobs/captain/tools/firecrawl_parser_job_spec.rb
index e12efc54bd0..6aed603855d 100644
--- a/spec/enterprise/jobs/captain/tools/firecrawl_parser_job_spec.rb
+++ b/spec/enterprise/jobs/captain/tools/firecrawl_parser_job_spec.rb
@@ -61,6 +61,16 @@ RSpec.describe Captain::Tools::FirecrawlParserJob, type: :job do
       end
     end
 
+    it 'stores external links longer than 255 characters' do
+      long_url = "https://example.com/#{'arabic-product-slug-' * 300}"
+      payload[:metadata]['url'] = long_url
+
+      described_class.perform_now(assistant_id: assistant.id, payload: payload)
+
+      expect(assistant.documents.last.external_link).to eq(long_url)
+      expect(assistant.documents.last.external_link.length).to be > 255
+    end
+
     context 'when an error occurs' do
       it 'raises an error with a descriptive message' do
         allow(Captain::Assistant).to receive(:find).and_raise(ActiveRecord::RecordNotFound)