diff --git a/.github/workflows/weekly-editors-health-check.lock.yml b/.github/workflows/weekly-editors-health-check.lock.yml
index c1fed13b07..4940401bf0 100644
--- a/.github/workflows/weekly-editors-health-check.lock.yml
+++ b/.github/workflows/weekly-editors-health-check.lock.yml
@@ -399,7 +399,7 @@ jobs:
           mkdir -p /tmp/gh-aw/safeoutputs
           mkdir -p /tmp/gh-aw/mcp-logs/safeoutputs
           cat > /opt/gh-aw/safeoutputs/config.json << 'GH_AW_SAFE_OUTPUTS_CONFIG_EOF'
-          {"create_pull_request":{"expires":168,"max":1},"missing_data":{},"missing_tool":{},"noop":{"max":1},"upload_asset":{"max":0}}
+          {"create_pull_request":{"expires":168,"max":1},"missing_data":{},"missing_tool":{},"noop":{"max":1},"upload_asset":{"max":5}}
           GH_AW_SAFE_OUTPUTS_CONFIG_EOF
           cat > /opt/gh-aw/safeoutputs/tools.json << 'GH_AW_SAFE_OUTPUTS_TOOLS_EOF'
           [
@@ -441,7 +441,7 @@ jobs:
               "name": "create_pull_request"
             },
             {
-              "description": "Upload a file as a URL-addressable asset that can be referenced in issues, PRs, or comments. The file is stored on an orphaned git branch and returns a permanent URL. Use this for images, diagrams, or other files that need to be embedded in GitHub content. CONSTRAINTS: Maximum file size: 10240KB. Allowed file extensions: [.png .jpg .jpeg].",
+              "description": "Upload a file as a URL-addressable asset that can be referenced in issues, PRs, or comments. The file is stored on an orphaned git branch and returns a permanent URL. Use this for images, diagrams, or other files that need to be embedded in GitHub content. CONSTRAINTS: Maximum 5 asset(s) can be uploaded. Maximum file size: 10240KB. Allowed file extensions: [.png .jpg .jpeg].",
               "inputSchema": {
                 "additionalProperties": false,
                 "properties": {
diff --git a/.github/workflows/weekly-editors-health-check.md b/.github/workflows/weekly-editors-health-check.md
index d0461b4d96..8031eea07e 100644
--- a/.github/workflows/weekly-editors-health-check.md
+++ b/.github/workflows/weekly-editors-health-check.md
@@ -33,6 +33,7 @@ tools:
 
 safe-outputs:
   upload-asset:
+    max: 5
   create-pull-request:
     title-prefix: "[docs] "
     labels: [documentation, automation]