diff --git a/.github/repository-settings.md b/.github/repository-settings.md
index f259eac5f..f1b76f075 100644
--- a/.github/repository-settings.md
+++ b/.github/repository-settings.md
@@ -18,6 +18,7 @@ settings](../docs/how-to-configure-new-repository.md#repository-settings).
   * EasyCLA
   * spelling-check
   * table-check
+  * toc-check
 
 ### `**/**`
 
diff --git a/.github/workflows/toc-check.yml b/.github/workflows/toc-check.yml
new file mode 100644
index 000000000..0661e22d1
--- /dev/null
+++ b/.github/workflows/toc-check.yml
@@ -0,0 +1,13 @@
+name: Table of contents checking
+
+on:
+  pull_request:
+
+jobs:
+  toc-check:
+    runs-on: ubuntu-latest
+    steps:
+      - uses: actions/checkout@v4
+
+      - name: check TOC in assets.md
+        run: make markdown-toc-check
diff --git a/Makefile b/Makefile
index 5d0ad8fb9..48667a8c2 100644
--- a/Makefile
+++ b/Makefile
@@ -8,7 +8,6 @@ export MSYS_NO_PATHCONV=1
 table-generation:
 	docker run --rm -v ${PWD}:/repo -w /repo python:3-alpine python ./scripts/update-sig-tables.py --install;
 
-
 validate-sigs:
 	docker run --rm -v ${PWD}:/repo -w /repo python:3-alpine python ./scripts/validate-sigs.py --install;
 
@@ -38,3 +37,6 @@ markdown-toc:
 			echo markdown-toc: no TOC markers, skipping $$f; \
 		fi; \
 	done
+
+markdown-toc-check: markdown-toc
+	git diff --exit-code ':*.md' || (echo 'Generated markdown Table of Contents is out of date, please run "make markdown-toc" and commit the changes in this PR.' && exit 1)
diff --git a/assets.md b/assets.md
index cb703dea3..d21ece2b3 100644
--- a/assets.md
+++ b/assets.md
@@ -13,6 +13,7 @@ This file is intended to list all the assets controlled by OpenTelemetry.
   * [Equinix bare metal runners](#equinix-bare-metal-runners)
   * [FOSSA](#fossa)
   * [GitHub Actions large runners](#github-actions-large-runners)
+  * [Google Cloud account](#google-cloud-account)
   * [Grafana organization for SIG Security](#grafana-organization-for-sig-security)
   * [Netlify](#netlify)
   * [Oracle Cloud account](#oracle-cloud-account)
@@ -25,6 +26,7 @@ This file is intended to list all the assets controlled by OpenTelemetry.
   * [PyPI](#pypi)
   * [PHP Extras](#php-extras)
 - [Communication channels](#communication-channels)
+  * [CNCF Community Group](#cncf-community-group)
   * [opentelemetry-calendar-contributors Google Group](#opentelemetry-calendar-contributors-google-group)
   * [OpenTelemetry Calendar Invites Google Group](#opentelemetry-calendar-invites-google-group)
   * [Mailing list cncf-opentelemetry-net-maintainers@lists.cncf.io](#mailing-list-cncf-opentelemetry-net-maintainerslistscncfio)
@@ -38,8 +40,9 @@ This file is intended to list all the assets controlled by OpenTelemetry.
 - [Bot accounts](#bot-accounts)
   * [Easy CLA](#easy-cla)
   * [Docker Hub](#docker-hub)
-  * [otelbot](#otelbot)
+  * [`otelbot`](#otelbot)
   * [OpenTelemetry Bot](#opentelemetry-bot)
+  * [Slack](#slack)
 - [Security](#security)
 
 <!-- tocstop -->