diff --git a/docs/modernization/debt.md b/docs/modernization/debt.md
index 125a430d..b9920120 100644
--- a/docs/modernization/debt.md
+++ b/docs/modernization/debt.md
@@ -18,6 +18,13 @@ agent or engineer to remove them without reconstructing context from chat.
 
 ## Recent Reductions
 
+- 2026-06-15: `DEBT-0038` was narrowed again. The retained cloud bulk-upload
+  per-file execution loop in `LegacyCloudServices::upload_all_bulk_files()`
+  now routes through a focused helper in `src/legacy_cloud_services.cpp`
+  instead of living inline in the retained service method; the remaining
+  cloud bridge debt stays concentrated in retained prompt/progress lifetime,
+  OpenGL context guarding, and the still-retained transfer-thread execution
+  model.
 - 2026-06-15: `DEBT-0038` was narrowed again. The retained cloud bulk-upload
   progress lifetime wiring in `LegacyCloudServices::begin_bulk_upload()` and
   `end_bulk_upload()` now routes through focused helpers in
diff --git a/docs/modernization/roadmap.md b/docs/modernization/roadmap.md
index 38e26bd7..eef1cca6 100644
--- a/docs/modernization/roadmap.md
+++ b/docs/modernization/roadmap.md
@@ -155,6 +155,12 @@ routes through focused helpers in `src/legacy_cloud_services.cpp`, so the
 remaining cloud bridge debt is further concentrated on retained
 prompt/progress lifetime, OpenGL context guarding, and the still-retained
 transfer-thread execution model.
+The retained cloud bulk-upload per-file execution loop in
+`LegacyCloudServices::upload_all_bulk_files()` now also routes through a
+focused helper in `src/legacy_cloud_services.cpp`, so the remaining cloud
+bridge debt is further concentrated on retained prompt/progress lifetime,
+OpenGL context guarding, and the still-retained transfer-thread execution
+model.
 
 Recent 2026-06-13 retained preview reductions continue to narrow DEBT-0036:
 `NodeStrokePreview::draw_stroke_immediate()` now also routes
diff --git a/docs/modernization/tasks.md b/docs/modernization/tasks.md
index 81a412eb..9607aca5 100644
--- a/docs/modernization/tasks.md
+++ b/docs/modernization/tasks.md
@@ -873,6 +873,41 @@ Completed Task Log:
 | --- | --- | ---: | --- | --- |
 | 2026-06-15 | ADP-022 | no score movement | `MSBuild.exe out\build\windows-msvc-default\panopainter_app.vcxproj /p:Configuration=Debug /p:Platform=x64`; `ctest --preset desktop-fast --build-config Debug -R "pp_app_core_document_cloud" --output-on-failure` | `df2c6783` |
 
+### ADP-023 - Extract Cloud Bulk Upload Loop Helper
+
+Status: Done
+Score: no score movement
+Debt: `DEBT-0038`
+Scope: `src/legacy_cloud_services.cpp` only
+
+Goal:
+
+Reduce the inline retained cloud bulk-upload execution surface by extracting
+the per-file upload loop from `LegacyCloudServices::upload_all_bulk_files()`
+into a focused helper while preserving current behavior.
+
+Done Checks:
+
+- The retained cloud bulk-upload per-file loop no longer lives inline in
+  `LegacyCloudServices::upload_all_bulk_files()`.
+- The retained bulk-upload execution path now routes through a focused helper
+  in `src/legacy_cloud_services.cpp`.
+- `DEBT-0038` and the roadmap note the reduced remaining cloud bridge
+  surface.
+
+Validation:
+
+```powershell
+& 'C:\Program Files\Microsoft Visual Studio\18\Community\MSBuild\Current\Bin\MSBuild.exe' out\build\windows-msvc-default\panopainter_app.vcxproj /p:Configuration=Debug /p:Platform=x64
+ctest --preset desktop-fast --build-config Debug -R "pp_app_core_document_cloud" --output-on-failure
+```
+
+Completed Task Log:
+
+| Date | Task | Score | Validation | Commit |
+| --- | --- | ---: | --- | --- |
+| 2026-06-15 | ADP-023 | no score movement | `MSBuild.exe out\build\windows-msvc-default\panopainter_app.vcxproj /p:Configuration=Debug /p:Platform=x64`; `ctest --preset desktop-fast --build-config Debug -R "pp_app_core_document_cloud" --output-on-failure` | `(pending)` |
+
 Completed Task Log:
 
 | Date | Task | Score | Validation | Commit |
diff --git a/src/legacy_cloud_services.cpp b/src/legacy_cloud_services.cpp
index 12394eae..cfe29bf3 100644
--- a/src/legacy_cloud_services.cpp
+++ b/src/legacy_cloud_services.cpp
@@ -218,6 +218,23 @@ std::shared_ptr<NodeProgressBar> create_cloud_bulk_upload_progress(
     return app.show_progress(progress_plan.title, progress_plan.total);
 }
 
+void execute_cloud_bulk_upload_files(
+    App& app,
+    const std::vector<std::string>& names,
+    const std::shared_ptr<NodeProgressBar>& bulk_progress)
+{
+    [[maybe_unused]] gl_state gl;
+    for (const auto& n : names)
+    {
+        std::string path = app.data_path + "/" + n;
+        execute_cloud_upload_transfer(app, path, std::string(), std::function<void(float)> {});
+
+        if (bulk_progress) {
+            bulk_progress->increment();
+        }
+    }
+}
+
 void close_cloud_bulk_upload_progress(std::shared_ptr<NodeProgressBar>& progress)
 {
     if (progress) {
@@ -275,16 +292,7 @@ public:
     void upload_all_bulk_files() override
     {
         auto names = Asset::list_files(app_.data_path, ".*\\.ppi");
-        [[maybe_unused]] gl_state gl;
-        for (const auto& n : names)
-        {
-            std::string path = app_.data_path + "/" + n;
-            execute_cloud_upload_transfer(app_, path, std::string(), std::function<void(float)> {});
-
-            if (bulk_progress_) {
-                bulk_progress_->increment();
-            }
-        }
+        execute_cloud_bulk_upload_files(app_, names, bulk_progress_);
     }
 
     void end_bulk_upload() override