diff --git a/.github/workflows/Breakage.yml b/.github/workflows/Breakage.yml
index b6f65fda..7853e16e 100644
--- a/.github/workflows/Breakage.yml
+++ b/.github/workflows/Breakage.yml
@@ -9,7 +9,14 @@ on:
 
 jobs:
   call:
-    if: contains(github.event.pull_request.labels.*.name, 'run breakage')
+    # A 'labeled' event fires once per label added, and re-evaluates against the PR's
+    # *current* full label set — so adding several labels in a row would otherwise
+    # re-run this job on every subsequent label add. Only react to 'labeled' when it's
+    # this specific label; for other trigger types (synchronize/reopened), fall back to
+    # checking the current label set as before.
+    if: >
+      (github.event.action == 'labeled' && github.event.label.name == 'run breakage') ||
+      (github.event.action != 'labeled' && contains(github.event.pull_request.labels.*.name, 'run breakage'))
     strategy:
       fail-fast: false
       matrix:
diff --git a/.github/workflows/CI.yml b/.github/workflows/CI.yml
index 0d8fb2af..9e4dda0b 100644
--- a/.github/workflows/CI.yml
+++ b/.github/workflows/CI.yml
@@ -10,7 +10,15 @@ on:
     
 jobs:
   call:
-    if: github.event_name != 'pull_request' || contains(github.event.pull_request.labels.*.name, 'run ci')
+    # A 'labeled' event fires once per label added, and re-evaluates against the PR's
+    # *current* full label set — so adding several labels in a row would otherwise
+    # re-run this job on every subsequent label add. Only react to 'labeled' when it's
+    # this specific label; for other trigger types (synchronize/reopened), fall back to
+    # checking the current label set as before.
+    if: >
+      github.event_name != 'pull_request' ||
+      (github.event.action == 'labeled' && github.event.label.name == 'run ci') ||
+      (github.event.action != 'labeled' && contains(github.event.pull_request.labels.*.name, 'run ci'))
     uses: control-toolbox/CTActions/.github/workflows/ci.yml@main
     with:
       runs_on: '["ubuntu-latest","macos-latest"]'
diff --git a/.github/workflows/Documentation.yml b/.github/workflows/Documentation.yml
index 9c99dad2..b309e06b 100644
--- a/.github/workflows/Documentation.yml
+++ b/.github/workflows/Documentation.yml
@@ -11,7 +11,15 @@ on:
   
 jobs:
   call:
-    if: github.event_name != 'pull_request' || contains(github.event.pull_request.labels.*.name, 'run documentation')
+    # A 'labeled' event fires once per label added, and re-evaluates against the PR's
+    # *current* full label set — so adding several labels in a row would otherwise
+    # re-run this job on every subsequent label add. Only react to 'labeled' when it's
+    # this specific label; for other trigger types (synchronize/reopened), fall back to
+    # checking the current label set as before.
+    if: >
+      github.event_name != 'pull_request' ||
+      (github.event.action == 'labeled' && github.event.label.name == 'run documentation') ||
+      (github.event.action != 'labeled' && contains(github.event.pull_request.labels.*.name, 'run documentation'))
     uses: control-toolbox/CTActions/.github/workflows/documentation.yml@main
     with:
       use_ct_registry: true