diff --git a/.github/workflows/ios_sentry_upload_adhoc.yml b/.github/workflows/ios_sentry_upload_adhoc.yml
index dd1d750d..defda50a 100644
--- a/.github/workflows/ios_sentry_upload_adhoc.yml
+++ b/.github/workflows/ios_sentry_upload_adhoc.yml
@@ -7,6 +7,7 @@ on:
 
 jobs:
   build_distribution:
+    if: github.event_name != 'pull_request' || github.head_ref != 'codex/test-sentry-cli-dsym-e2e'
     runs-on: macos-26
 
     defaults:
diff --git a/.github/workflows/ios_sentry_upload_pr.yml b/.github/workflows/ios_sentry_upload_pr.yml
index 255a119d..c5fa19f2 100644
--- a/.github/workflows/ios_sentry_upload_pr.yml
+++ b/.github/workflows/ios_sentry_upload_pr.yml
@@ -19,6 +19,19 @@ jobs:
         with:
           fetch-depth: 0
 
+      - name: Checkout sentry-cli
+        uses: actions/checkout@v6
+        with:
+          repository: getsentry/sentry-cli
+          ref: c596fcddd616867b6c6cdfa11f9853dc889a585a
+          path: sentry-cli
+
+      - name: Build sentry-cli
+        working-directory: ${{ github.workspace }}/sentry-cli
+        run: |
+          rustup target add aarch64-apple-darwin
+          cargo build --release --locked --target aarch64-apple-darwin
+
       - name: Set up Ruby env
         uses: ruby/setup-ruby@v1
         with:
@@ -43,6 +56,9 @@ jobs:
           ASC_KEY: ${{ secrets.ASC_PRIVATE_KEY }}
           SIGNING_KEY_PASSWORD: ${{ secrets.IOS_DIST_SIGNING_KEY_PASSWORD }}
           SIGNING_KEY_FILE_PATH: signing-cert.p12
+          SENTRY_AUTH_TOKEN: ${{ secrets.SENTRY_SENTRY_AUTH_TOKEN }}
+          SENTRY_CLI_PATH: ${{ github.workspace }}/sentry-cli/target/aarch64-apple-darwin/release/sentry-cli
+          SENTRY_LOG_LEVEL: debug
           SENTRY_SENTRY_AUTH_TOKEN: ${{ secrets.SENTRY_SENTRY_AUTH_TOKEN }}
           APPLE_TEAM_ID: ${{ secrets.APPLE_TEAM_ID }}
           CONFIGURATION: Release
diff --git a/.github/workflows/ios_sentry_upload_snapshots.yml b/.github/workflows/ios_sentry_upload_snapshots.yml
index b5b8ad59..4d42e135 100644
--- a/.github/workflows/ios_sentry_upload_snapshots.yml
+++ b/.github/workflows/ios_sentry_upload_snapshots.yml
@@ -21,6 +21,7 @@ jobs:
   # Build the snapshot test bundle once on a single runner, then share the
   # products with downstream simulator jobs via an artifact.
   build_for_testing:
+    if: github.event_name != 'pull_request' || github.head_ref != 'codex/test-sentry-cli-dsym-e2e'
     runs-on: macos-26
 
     env:
@@ -209,4 +210,4 @@ jobs:
       - name: Upload snapshots to Sentry
         env:
           SENTRY_SENTRY_AUTH_TOKEN: ${{ secrets.SENTRY_SENTRY_AUTH_TOKEN }}
-        run: bundle exec fastlane ios upload_sentry_snapshots path:"${SNAPSHOT_UPLOAD_BASE_DIR}"
\ No newline at end of file
+        run: bundle exec fastlane ios upload_sentry_snapshots path:"${SNAPSHOT_UPLOAD_BASE_DIR}"
diff --git a/.github/workflows/ios_sentry_upload_swift_snapshots.yml b/.github/workflows/ios_sentry_upload_swift_snapshots.yml
index e93ddccf..bf32ab7d 100644
--- a/.github/workflows/ios_sentry_upload_swift_snapshots.yml
+++ b/.github/workflows/ios_sentry_upload_swift_snapshots.yml
@@ -9,6 +9,7 @@ on:
 
 jobs:
   upload_sentry_swift_snapshots:
+    if: github.event_name != 'pull_request' || github.head_ref != 'codex/test-sentry-cli-dsym-e2e'
     runs-on: macos-26
 
     defaults:
diff --git a/ios/Gemfile.lock b/ios/Gemfile.lock
index 87d4f76e..4644a64e 100644
--- a/ios/Gemfile.lock
+++ b/ios/Gemfile.lock
@@ -1,3 +1,11 @@
+GIT
+  remote: https://github.com/getsentry/sentry-fastlane-plugin.git
+  revision: 0fe84e64455d7f6643976368c04a5496b1a3f263
+  branch: codex/ipa-dsym-build-upload
+  specs:
+    fastlane-plugin-sentry (2.6.2)
+      os (~> 1.1, >= 1.1.4)
+
 GEM
   remote: https://rubygems.org/
   specs:
@@ -123,8 +131,6 @@ GEM
       xcodeproj (>= 1.13.0, < 2.0.0)
       xcpretty (~> 0.4.1)
       xcpretty-travis-formatter (>= 0.0.3, < 2.0.0)
-    fastlane-plugin-sentry (2.5.2)
-      os (~> 1.1, >= 1.1.4)
     fastlane-sirp (1.1.0)
     gh_inspector (1.1.3)
     google-apis-androidpublisher_v3 (0.102.0)
@@ -242,7 +248,7 @@ PLATFORMS
 
 DEPENDENCIES
   fastlane
-  fastlane-plugin-sentry (>= 2.5.1, < 3.0.0)
+  fastlane-plugin-sentry (>= 2.5.1, < 3.0.0)!
   xcpretty
 
 BUNDLED WITH
diff --git a/ios/fastlane/Fastfile b/ios/fastlane/Fastfile
index c1944c97..9a5b555f 100644
--- a/ios/fastlane/Fastfile
+++ b/ios/fastlane/Fastfile
@@ -186,19 +186,41 @@ platform :ios do
     prepare_signing
     build_app_for_scheme
     ipa_path = export_thinned_size_analysis_ipa
-    xcarchive_path = lane_context[SharedValues::XCODEBUILD_ARCHIVE]
-    replace_xcarchive_app_with_ipa(
-      ipa_path: ipa_path,
-      xcarchive_path: xcarchive_path
-    )
-    sentry_upload_build(
-      auth_token: ENV['SENTRY_SENTRY_AUTH_TOKEN'],
-      org_slug: 'sentry',
-      project_slug: 'hackernews-ios',
-      xcarchive_path: xcarchive_path,
-      build_configuration: 'Release',
-      log_level: 'debug'
+    xcarchive_path = File.expand_path(
+      lane_context[SharedValues::XCODEBUILD_ARCHIVE],
+      File.expand_path('..', __dir__)
     )
+
+    if ENV['SENTRY_CLI_PATH']
+      dsym_path = File.join(xcarchive_path, 'dSYMs')
+      UI.important(
+        "Testing IPA+dSYM upload through fastlane-plugin-sentry with #{ENV.fetch('SENTRY_CLI_PATH')}: " \
+        "IPA=#{ipa_path}, dSYMs=#{dsym_path}"
+      )
+      sentry_upload_build(
+        auth_token: ENV['SENTRY_SENTRY_AUTH_TOKEN'],
+        org_slug: 'sentry',
+        project_slug: 'hackernews-ios',
+        ipa_path: ipa_path,
+        dsym_path: dsym_path,
+        sentry_cli_path: ENV.fetch('SENTRY_CLI_PATH'),
+        build_configuration: 'Release-dsym-e2e',
+        log_level: 'debug'
+      )
+    else
+      replace_xcarchive_app_with_ipa(
+        ipa_path: ipa_path,
+        xcarchive_path: xcarchive_path
+      )
+      sentry_upload_build(
+        auth_token: ENV['SENTRY_SENTRY_AUTH_TOKEN'],
+        org_slug: 'sentry',
+        project_slug: 'hackernews-ios',
+        xcarchive_path: xcarchive_path,
+        build_configuration: 'Release',
+        log_level: 'debug'
+      )
+    end
   end
 
   desc 'Export a thinned Release IPA for Sentry Size Analysis'
diff --git a/ios/fastlane/Pluginfile b/ios/fastlane/Pluginfile
index 521e6116..001bc6ae 100644
--- a/ios/fastlane/Pluginfile
+++ b/ios/fastlane/Pluginfile
@@ -2,4 +2,6 @@
 #
 # Ensure this file is checked in to source control!
 
-gem 'fastlane-plugin-sentry', '>= 2.5.1', '< 3.0.0'
+gem 'fastlane-plugin-sentry', '>= 2.5.1', '< 3.0.0',
+    git: 'https://github.com/getsentry/sentry-fastlane-plugin.git',
+    branch: 'codex/ipa-dsym-build-upload'