diff --git a/.github/dependabot.yml b/.github/dependabot.yml
index 41f0e18b..0dfceda4 100644
--- a/.github/dependabot.yml
+++ b/.github/dependabot.yml
@@ -1,22 +1,31 @@
 version: 2
+multi-ecosystem-groups:
+  ci-tooling:
+    schedule:
+      interval: monthly
+    assignees:
+      - camUrban
 updates:
   - package-ecosystem: github-actions
     directory: /
-    schedule:
-      interval: weekly
+    patterns:
+      - "*"
+    multi-ecosystem-group: ci-tooling
     cooldown:
       default-days: 7
-    groups:
-      actions:
-        patterns:
-          - "*"
   - package-ecosystem: pre-commit
     directory: /
-    schedule:
-      interval: weekly
+    patterns:
+      - "*"
+    multi-ecosystem-group: ci-tooling
     cooldown:
       default-days: 7
-    groups:
-      pre-commit:
-        patterns:
-          - "*"
+  - package-ecosystem: pip
+    directory: /
+    schedule:
+      interval: monthly
+    open-pull-requests-limit: 0
+    labels:
+      - dependencies
+    assignees:
+      - camUrban
diff --git a/.github/workflows/dependabot-triage.yml b/.github/workflows/dependabot-triage.yml
new file mode 100644
index 00000000..b69812bf
--- /dev/null
+++ b/.github/workflows/dependabot-triage.yml
@@ -0,0 +1,47 @@
+name: dependabot-triage
+
+on:
+  pull_request:
+    types: [opened, reopened, synchronize]
+
+permissions: {}
+
+jobs:
+  dependabot-triage:
+    if: github.event.pull_request.user.login == 'dependabot[bot]'
+    runs-on: ubuntu-latest
+    permissions:
+      issues: write
+      pull-requests: write
+    steps:
+      - name: Shorten the pull request title
+        env:
+          GH_TOKEN: ${{ github.token }}
+          PR_URL: ${{ github.event.pull_request.html_url }}
+        run: |
+          non_ci_files=$(gh pr view "$PR_URL" --json files --jq '[.files[].path | select(startswith(".github/") or . == ".pre-commit-config.yaml" | not)] | length')
+          if [ "$non_ci_files" -eq 0 ]; then
+            title="Bump CI tooling"
+          else
+            dependency_count=$(gh pr view "$PR_URL" --json commits --jq '[.commits[] | select(any(.authors[]; .login == "dependabot[bot]")) | .messageBody | split("\n")[] | select(startswith("- dependency-name: "))] | unique | length')
+            if [ "$dependency_count" -eq 1 ]; then
+              title="Bump runtime dependency"
+            else
+              title="Bump runtime dependencies"
+            fi
+          fi
+          gh pr edit "$PR_URL" --title "$title"
+      - name: Set the milestone to the lowest open release
+        env:
+          GH_TOKEN: ${{ github.token }}
+          PR_URL: ${{ github.event.pull_request.html_url }}
+          REPO: ${{ github.repository }}
+        run: |
+          has_milestone=$(gh pr view "$PR_URL" --json milestone --jq '.milestone != null')
+          if [ "$has_milestone" = "true" ]; then
+            exit 0
+          fi
+          milestone=$(gh api "repos/$REPO/milestones?state=open&per_page=100" --jq '[.[].title | select(test("^v[0-9]+\\.[0-9]+\\.[0-9]+$"))] | sort_by(ltrimstr("v") | split(".") | map(tonumber)) | first // empty')
+          if [ -n "$milestone" ]; then
+            gh pr edit "$PR_URL" --milestone "$milestone"
+          fi
diff --git a/CLAUDE.md b/CLAUDE.md
index e093acc0..c364150d 100644
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -34,7 +34,7 @@ Requires Python 3.11, but active development is done in 3.14
 
 ### Relevant Directories, Packages, and Files
 
-- `.github/`: Directory with GitHub configuration files: the issue and pull request templates, the label definitions (`labels.yml`), the Dependabot, funding, and code-owner configuration, and the GitHub Actions workflows (`ascii-only.yml`, `ci.yml`, `label-sync.yml`, `pre-commit-hooks.yml`, `private-access.yml`, `publish.yml`, and `zizmor.yml`)
+- `.github/`: Directory with GitHub configuration files: the issue and pull request templates, the label definitions (`labels.yml`), the Dependabot, funding, and code-owner configuration, and the GitHub Actions workflows (`ascii-only.yml`, `ci.yml`, `dependabot-triage.yml`, `label-sync.yml`, `pre-commit-hooks.yml`, `private-access.yml`, `publish.yml`, and `zizmor.yml`)
 - `.venv/`: Directory for the Python virtual environment, configured for the host machine's OS (not included in version control)
 - `.venv-wsl/`: Directory for the Python virtual environment configured for a WSL OS (not included in version control, may be missing if host machine doesn't use WSL for development)
 - `experimental/`: Directory with experimental scripts and prototypes (not included in version control)