diff --git a/.github/workflows/annocheck.yml b/.github/workflows/annocheck.yml
index 211dfbdac4744e..76489f1885263b 100644
--- a/.github/workflows/annocheck.yml
+++ b/.github/workflows/annocheck.yml
@@ -40,7 +40,12 @@ jobs:
       image: ghcr.io/ruby/ruby-ci-image:gcc-11
       options: --user root
 
-    if: ${{ !contains(github.event.head_commit.message, '[DOC]') && !contains(github.event.pull_request.labels.*.name, 'Documentation') }}
+    if: >-
+      ${{!(false
+      || contains(github.event.head_commit.message, '[DOC]')
+      || contains(github.event.pull_request.title, '[DOC]')
+      || contains(github.event.pull_request.labels.*.name, 'Documentation')
+      )}}
 
     env:
       CONFIGURE_TTY: never
diff --git a/.github/workflows/baseruby.yml b/.github/workflows/baseruby.yml
index 7d461fa8094cda..b5455f5bc9a885 100644
--- a/.github/workflows/baseruby.yml
+++ b/.github/workflows/baseruby.yml
@@ -36,7 +36,12 @@ jobs:
 
     runs-on: ubuntu-20.04
 
-    if: ${{ !contains(github.event.head_commit.message, '[DOC]') && !contains(github.event.pull_request.labels.*.name, 'Documentation') }}
+    if: >-
+      ${{!(false
+      || contains(github.event.head_commit.message, '[DOC]')
+      || contains(github.event.pull_request.title, '[DOC]')
+      || contains(github.event.pull_request.labels.*.name, 'Documentation')
+      )}}
 
     strategy:
       matrix:
diff --git a/.github/workflows/check_dependencies.yml b/.github/workflows/check_dependencies.yml
index 29bd489efc9f73..65ba10b7a2ebd7 100644
--- a/.github/workflows/check_dependencies.yml
+++ b/.github/workflows/check_dependencies.yml
@@ -38,7 +38,12 @@ jobs:
 
     runs-on: ${{ matrix.os }}
 
-    if: ${{ !contains(github.event.head_commit.message, '[DOC]') && !contains(github.event.pull_request.labels.*.name, 'Documentation') }}
+    if: >-
+      ${{!(false
+      || contains(github.event.head_commit.message, '[DOC]')
+      || contains(github.event.pull_request.title, '[DOC]')
+      || contains(github.event.pull_request.labels.*.name, 'Documentation')
+      )}}
 
     steps:
       - uses: actions/checkout@c85c95e3d7251135ab7dc9ce3241c5835cc595a9 # v3.5.3
diff --git a/.github/workflows/codeql-analysis.yml b/.github/workflows/codeql-analysis.yml
index 768eb01d777a03..28142e8e0e8ef4 100644
--- a/.github/workflows/codeql-analysis.yml
+++ b/.github/workflows/codeql-analysis.yml
@@ -36,7 +36,12 @@ jobs:
       contents: read # for actions/checkout to fetch code
       security-events: write # for github/codeql-action/autobuild to send a status report
     # CodeQL fails to run pull requests from dependabot due to missing write access to upload results.
-    if: ${{ !contains(github.event.head_commit.message, '[DOC]') && !contains(github.event.pull_request.labels.*.name, 'Documentation') && github.event.head_commit.pusher.name != 'dependabot[bot]' }}
+    if: >-
+      ${{!(false
+      || contains(github.event.head_commit.message, '[DOC]')
+      || contains(github.event.pull_request.title, '[DOC]')
+      || contains(github.event.pull_request.labels.*.name, 'Documentation')
+      )}}
 
     env:
       enable_install_doc: no
diff --git a/.github/workflows/compilers.yml b/.github/workflows/compilers.yml
index cb87c6601db1e2..56cdaf2bb0d072 100644
--- a/.github/workflows/compilers.yml
+++ b/.github/workflows/compilers.yml
@@ -218,7 +218,12 @@ jobs:
       image: ghcr.io/ruby/ruby-ci-image:${{ matrix.entry.container || matrix.entry.env.default_cc || 'clang-16' }}
       options: --user root
 
-    if: ${{ !contains(github.event.head_commit.message, '[DOC]') && !contains(github.event.pull_request.labels.*.name, 'Documentation') }}
+    if: >-
+      ${{!(false
+      || contains(github.event.head_commit.message, '[DOC]')
+      || contains(github.event.pull_request.title, '[DOC]')
+      || contains(github.event.pull_request.labels.*.name, 'Documentation')
+      )}}
 
     env: ${{ matrix.entry.env || matrix.env }}
 
diff --git a/.github/workflows/macos.yml b/.github/workflows/macos.yml
index f6d5c2cc6a5f55..16d4199ea214b3 100644
--- a/.github/workflows/macos.yml
+++ b/.github/workflows/macos.yml
@@ -47,7 +47,12 @@ jobs:
 
     runs-on: ${{ matrix.os }}
 
-    if: ${{ !contains(github.event.head_commit.message, '[DOC]') && !contains(github.event.pull_request.labels.*.name, 'Documentation') }}
+    if: >-
+      ${{!(false
+      || contains(github.event.head_commit.message, '[DOC]')
+      || contains(github.event.pull_request.title, '[DOC]')
+      || contains(github.event.pull_request.labels.*.name, 'Documentation')
+      )}}
 
     steps:
       - uses: actions/checkout@c85c95e3d7251135ab7dc9ce3241c5835cc595a9 # v3.5.3
diff --git a/.github/workflows/mingw.yml b/.github/workflows/mingw.yml
index 2017c478fd08c5..b7387d0fcf23ce 100644
--- a/.github/workflows/mingw.yml
+++ b/.github/workflows/mingw.yml
@@ -58,7 +58,12 @@ jobs:
             test-all-opts: '--name=!/TestObjSpace#test_reachable_objects_during_iteration/'
       fail-fast: false
 
-    if: ${{ !contains(github.event.head_commit.message, '[DOC]') && !contains(github.event.pull_request.labels.*.name, 'Documentation') }}
+    if: >-
+      ${{!(false
+      || contains(github.event.head_commit.message, '[DOC]')
+      || contains(github.event.pull_request.title, '[DOC]')
+      || contains(github.event.pull_request.labels.*.name, 'Documentation')
+      )}}
 
     steps:
       - name: Set up Ruby & MSYS2
diff --git a/.github/workflows/rjit-bindgen.yml b/.github/workflows/rjit-bindgen.yml
index 3c8043b9b46597..cb777c069755ea 100644
--- a/.github/workflows/rjit-bindgen.yml
+++ b/.github/workflows/rjit-bindgen.yml
@@ -39,7 +39,12 @@ jobs:
 
     runs-on: ubuntu-20.04
 
-    if: ${{ !contains(github.event.head_commit.message, '[DOC]') && !contains(github.event.pull_request.labels.*.name, 'Documentation') }}
+    if: >-
+      ${{!(false
+      || contains(github.event.head_commit.message, '[DOC]')
+      || contains(github.event.pull_request.title, '[DOC]')
+      || contains(github.event.pull_request.labels.*.name, 'Documentation')
+      )}}
 
     steps:
       - name: Set up Ruby
diff --git a/.github/workflows/rjit.yml b/.github/workflows/rjit.yml
index 22aa69570952bc..4d9062f1bd79ad 100644
--- a/.github/workflows/rjit.yml
+++ b/.github/workflows/rjit.yml
@@ -49,7 +49,12 @@ jobs:
 
     runs-on: ubuntu-22.04
 
-    if: ${{ !contains(github.event.head_commit.message, '[DOC]') && !contains(github.event.pull_request.labels.*.name, 'Documentation') }}
+    if: >-
+      ${{!(false
+      || contains(github.event.head_commit.message, '[DOC]')
+      || contains(github.event.pull_request.title, '[DOC]')
+      || contains(github.event.pull_request.labels.*.name, 'Documentation')
+      )}}
 
     steps:
       - uses: actions/checkout@c85c95e3d7251135ab7dc9ce3241c5835cc595a9 # v3.5.3
diff --git a/.github/workflows/spec_guards.yml b/.github/workflows/spec_guards.yml
index 79d375c703e029..4a5ff9a90fb087 100644
--- a/.github/workflows/spec_guards.yml
+++ b/.github/workflows/spec_guards.yml
@@ -27,7 +27,12 @@ jobs:
 
     runs-on: ubuntu-20.04
 
-    if: ${{ !contains(github.event.head_commit.message, '[DOC]') && !contains(github.event.pull_request.labels.*.name, 'Documentation') }}
+    if: >-
+      ${{!(false
+      || contains(github.event.head_commit.message, '[DOC]')
+      || contains(github.event.pull_request.title, '[DOC]')
+      || contains(github.event.pull_request.labels.*.name, 'Documentation')
+      )}}
 
     strategy:
       matrix:
diff --git a/.github/workflows/ubuntu.yml b/.github/workflows/ubuntu.yml
index 7f50e25dfafd6a..2e3f228aec6805 100644
--- a/.github/workflows/ubuntu.yml
+++ b/.github/workflows/ubuntu.yml
@@ -55,7 +55,12 @@ jobs:
 
     runs-on: ubuntu-20.04
 
-    if: ${{ !contains(github.event.head_commit.message, '[DOC]') && !contains(github.event.pull_request.labels.*.name, 'Documentation') }}
+    if: >-
+      ${{!(false
+      || contains(github.event.head_commit.message, '[DOC]')
+      || contains(github.event.pull_request.title, '[DOC]')
+      || contains(github.event.pull_request.labels.*.name, 'Documentation')
+      )}}
 
     steps:
       - uses: actions/checkout@c85c95e3d7251135ab7dc9ce3241c5835cc595a9 # v3.5.3
diff --git a/.github/workflows/wasm.yml b/.github/workflows/wasm.yml
index f40543a5389d75..496d5fc8925c4f 100644
--- a/.github/workflows/wasm.yml
+++ b/.github/workflows/wasm.yml
@@ -54,7 +54,12 @@ jobs:
 
     runs-on: ubuntu-20.04
 
-    if: ${{ !contains(github.event.head_commit.message, '[DOC]') && !contains(github.event.pull_request.labels.*.name, 'Documentation') }}
+    if: >-
+      ${{!(false
+      || contains(github.event.head_commit.message, '[DOC]')
+      || contains(github.event.pull_request.title, '[DOC]')
+      || contains(github.event.pull_request.labels.*.name, 'Documentation')
+      )}}
 
     steps:
       - uses: actions/checkout@c85c95e3d7251135ab7dc9ce3241c5835cc595a9 # v3.5.3
diff --git a/.github/workflows/windows.yml b/.github/workflows/windows.yml
index 2f706c09f264f4..0c02de78580494 100644
--- a/.github/workflows/windows.yml
+++ b/.github/workflows/windows.yml
@@ -40,7 +40,12 @@ jobs:
 
     runs-on: windows-${{ matrix.vs < 2022 && '2019' || matrix.vs }}
 
-    if: ${{ !contains(github.event.head_commit.message, '[DOC]') && !contains(github.event.pull_request.labels.*.name, 'Documentation') }}
+    if: >-
+      ${{!(false
+      || contains(github.event.head_commit.message, '[DOC]')
+      || contains(github.event.pull_request.title, '[DOC]')
+      || contains(github.event.pull_request.labels.*.name, 'Documentation')
+      )}}
 
     name: VisualStudio ${{ matrix.vs }}
 
diff --git a/.github/workflows/yjit-ubuntu.yml b/.github/workflows/yjit-ubuntu.yml
index b273fd6ac3faed..b9660f6aca9b2f 100644
--- a/.github/workflows/yjit-ubuntu.yml
+++ b/.github/workflows/yjit-ubuntu.yml
@@ -109,7 +109,12 @@ jobs:
 
     runs-on: ubuntu-20.04
 
-    if: ${{ !contains(github.event.head_commit.message, '[DOC]') && !contains(github.event.pull_request.labels.*.name, 'Documentation') }}
+    if: >-
+      ${{!(false
+      || contains(github.event.head_commit.message, '[DOC]')
+      || contains(github.event.pull_request.title, '[DOC]')
+      || contains(github.event.pull_request.labels.*.name, 'Documentation')
+      )}}
 
     steps:
       - uses: actions/checkout@c85c95e3d7251135ab7dc9ce3241c5835cc595a9 # v3.5.3