diff --git a/.github/workflows/release.yaml b/.github/workflows/release.yaml
index 94d7b6f9ae5e4..040054eb84cbc 100644
--- a/.github/workflows/release.yaml
+++ b/.github/workflows/release.yaml
@@ -924,3 +924,55 @@ jobs:
         continue-on-error: true
         run: |
           make sqlc-push
+
+  update-calendar:
+    name: "Update release calendar in docs"
+    runs-on: "ubuntu-latest"
+    needs: [release, publish-homebrew, publish-winget, publish-sqlc]
+    if: ${{ !inputs.dry_run }}
+    permissions:
+      contents: write
+      pull-requests: write
+    steps:
+      - name: Harden Runner
+        uses: step-security/harden-runner@c6295a65d1254861815972266d5933fd6e532bdf # v2.11.1
+        with:
+          egress-policy: audit
+
+      - name: Checkout repository
+        uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
+        with:
+          fetch-depth: 0 # Needed to get all tags for version calculation
+
+      - name: Set up Git
+        run: |
+          git config user.name "Coder CI"
+          git config user.email "cdrci@coder.com"
+
+      - name: Run update script
+        run: |
+          ./scripts/update-release-calendar.sh
+          make fmt/markdown
+
+      - name: Check for changes
+        id: check_changes
+        run: |
+          if git diff --quiet docs/install/releases/index.md; then
+            echo "No changes detected in release calendar."
+            echo "changes=false" >> $GITHUB_OUTPUT
+          else
+            echo "Changes detected in release calendar."
+            echo "changes=true" >> $GITHUB_OUTPUT
+          fi
+
+      - name: Create Pull Request
+        if: steps.check_changes.outputs.changes == 'true'
+        uses: peter-evans/create-pull-request@ff45666b9427631e3450c54a1bcbee4d9ff4d7c0 # v3.0.0
+        with:
+          commit-message: "docs: update release calendar"
+          title: "docs: update release calendar"
+          body: |
+            This PR automatically updates the release calendar in the docs.
+          branch: bot/update-release-calendar
+          delete-branch: true
+          labels: docs
diff --git a/docs/install/releases/index.md b/docs/install/releases/index.md
index d0ab0d1a05d5e..09aca9f37cb9b 100644
--- a/docs/install/releases/index.md
+++ b/docs/install/releases/index.md
@@ -53,18 +53,18 @@ Best practices for installing Coder can be found on our [install](../index.md)
 pages.
 
 ## Release schedule
-
-| Release name | Release Date       | Status           |
-|--------------|--------------------|------------------|
-| 2.12.x       | June 04, 2024      | Not Supported    |
-| 2.13.x       | July 02, 2024      | Not Supported    |
-| 2.14.x       | August 06, 2024    | Not Supported    |
-| 2.15.x       | September 03, 2024 | Not Supported    |
-| 2.16.x       | October 01, 2024   | Not Supported    |
-| 2.17.x       | November 05, 2024  | Not Supported    |
-| 2.18.x       | December 03, 2024  | Security Support |
-| 2.19.x       | February 04, 2024  | Stable           |
-| 2.20.x       | March 05, 2024     | Mainline         |
+<!-- Autogenerated release calendar from scripts/update-release-calendar.sh -->
+<!-- RELEASE_CALENDAR_START -->
+| Release name                                   | Release Date      | Status           | Latest Release                                                 |
+|------------------------------------------------|-------------------|------------------|----------------------------------------------------------------|
+| [2.16](https://coder.com/changelog/coder-2-16) | November 05, 2024 | Not Supported    | [v2.16.1](https://github.com/coder/coder/releases/tag/v2.16.1) |
+| [2.17](https://coder.com/changelog/coder-2-17) | December 03, 2024 | Not Supported    | [v2.17.3](https://github.com/coder/coder/releases/tag/v2.17.3) |
+| [2.18](https://coder.com/changelog/coder-2-18) | February 04, 2025 | Not Supported    | [v2.18.5](https://github.com/coder/coder/releases/tag/v2.18.5) |
+| [2.19](https://coder.com/changelog/coder-2-19) | February 04, 2025 | Security Support | [v2.19.1](https://github.com/coder/coder/releases/tag/v2.19.1) |
+| [2.20](https://coder.com/changelog/coder-2-20) | March 04, 2025    | Stable           | [v2.20.2](https://github.com/coder/coder/releases/tag/v2.20.2) |
+| [2.21](https://coder.com/changelog/coder-2-21) | April 01, 2025    | Mainline         | [v2.21.1](https://github.com/coder/coder/releases/tag/v2.21.1) |
+| 2.22                                           | May 07, 2024      | Not Released     | N/A                                                            |
+<!-- RELEASE_CALENDAR_END -->
 
 > [!TIP]
 > We publish a
diff --git a/scripts/update-release-calendar.sh b/scripts/update-release-calendar.sh
new file mode 100755
index 0000000000000..a9fe6e54d605d
--- /dev/null
+++ b/scripts/update-release-calendar.sh
@@ -0,0 +1,205 @@
+#!/bin/bash
+
+set -euo pipefail
+
+# This script automatically updates the release calendar in docs/install/releases/index.md
+# It calculates the releases based on the first Tuesday of each month rule
+# and updates the status of each release (Not Supported, Security Support, Stable, Mainline, Not Released)
+
+DOCS_FILE="docs/install/releases/index.md"
+
+# Define unique markdown comments as anchors
+CALENDAR_START_MARKER="<!-- RELEASE_CALENDAR_START -->"
+CALENDAR_END_MARKER="<!-- RELEASE_CALENDAR_END -->"
+
+# Get current date
+current_date=$(date +"%Y-%m-%d")
+current_month=$(date +"%m")
+current_year=$(date +"%Y")
+
+# Function to get the first Tuesday of a given month and year
+get_first_tuesday() {
+	local year=$1
+	local month=$2
+	local first_day
+	local days_until_tuesday
+	local first_tuesday
+
+	# Find the first day of the month
+	first_day=$(date -d "$year-$month-01" +"%u")
+
+	# Calculate days until first Tuesday (if day 1 is Tuesday, first_day=2)
+	days_until_tuesday=$((first_day == 2 ? 0 : (9 - first_day) % 7))
+
+	# Get the date of the first Tuesday
+	first_tuesday=$(date -d "$year-$month-01 +$days_until_tuesday days" +"%Y-%m-%d")
+
+	echo "$first_tuesday"
+}
+
+# Function to format date as "Month DD, YYYY"
+format_date() {
+	date -d "$1" +"%B %d, %Y"
+}
+
+# Function to get the latest patch version for a minor release
+get_latest_patch() {
+	local version_major=$1
+	local version_minor=$2
+	local tags
+	local latest
+
+	# Get all tags for this minor version
+	tags=$(cd "$(git rev-parse --show-toplevel)" && git tag | grep "^v$version_major\\.$version_minor\\." | sort -V)
+
+	# Get the latest one
+	latest=$(echo "$tags" | tail -1)
+
+	if [ -z "$latest" ]; then
+		# If no tags found, return empty
+		echo ""
+	else
+		# Return without the v prefix
+		echo "${latest#v}"
+	fi
+}
+
+# Generate releases table showing:
+# - 3 previous unsupported releases
+# - 1 security support release (n-2)
+# - 1 stable release (n-1)
+# - 1 mainline release (n)
+# - 1 next release (n+1)
+generate_release_calendar() {
+	local result=""
+	local version_major=2
+	local latest_version
+	local version_minor
+	local start_minor
+
+	# Find the current minor version by looking at the last mainline release tag
+	latest_version=$(cd "$(git rev-parse --show-toplevel)" && git tag | grep '^v[0-9]*\.[0-9]*\.[0-9]*$' | sort -V | tail -1)
+	version_minor=$(echo "$latest_version" | cut -d. -f2)
+
+	# Start with 3 unsupported releases back
+	start_minor=$((version_minor - 5))
+
+	# Initialize the calendar table with an additional column for latest release
+	result="| Release name | Release Date | Status | Latest Release |\n"
+	result+="|--------------|--------------|--------|----------------|\n"
+
+	# Generate rows for each release (7 total: 3 unsupported, 1 security, 1 stable, 1 mainline, 1 next)
+	for i in {0..6}; do
+		# Calculate release minor version
+		local rel_minor=$((start_minor + i))
+		# Format release name without the .x
+		local version_name="$version_major.$rel_minor"
+		local release_date
+		local formatted_date
+		local latest_patch
+		local patch_link
+		local status
+		local formatted_version_name
+
+		# Calculate release month and year based on release pattern
+		# This is a simplified calculation assuming monthly releases
+		local rel_month=$(((current_month - (5 - i) + 12) % 12))
+		[[ $rel_month -eq 0 ]] && rel_month=12
+		local rel_year=$current_year
+		if [[ $rel_month -gt $current_month ]]; then
+			rel_year=$((rel_year - 1))
+		fi
+		if [[ $rel_month -lt $current_month && $i -gt 5 ]]; then
+			rel_year=$((rel_year + 1))
+		fi
+
+		# Skip January releases starting from 2025
+		if [[ $rel_month -eq 1 && $rel_year -ge 2025 ]]; then
+			rel_month=2
+			# No need to reassign rel_year to itself
+		fi
+
+		# Get release date (first Tuesday of the month)
+		release_date=$(get_first_tuesday "$rel_year" "$(printf "%02d" "$rel_month")")
+		formatted_date=$(format_date "$release_date")
+
+		# Get latest patch version
+		latest_patch=$(get_latest_patch "$version_major" "$rel_minor")
+		if [ -n "$latest_patch" ]; then
+			patch_link="[v${latest_patch}](https://github.com/coder/coder/releases/tag/v${latest_patch})"
+		else
+			patch_link="N/A"
+		fi
+
+		# Determine status
+		if [[ "$release_date" > "$current_date" ]]; then
+			status="Not Released"
+		elif [[ $i -eq 6 ]]; then
+			status="Not Released"
+		elif [[ $i -eq 5 ]]; then
+			status="Mainline"
+		elif [[ $i -eq 4 ]]; then
+			status="Stable"
+		elif [[ $i -eq 3 ]]; then
+			status="Security Support"
+		else
+			status="Not Supported"
+		fi
+
+		# Format version name and patch link based on release status
+		# No links for unreleased versions
+		if [[ "$status" == "Not Released" ]]; then
+			formatted_version_name="$version_name"
+			patch_link="N/A"
+		else
+			formatted_version_name="[$version_name](https://coder.com/changelog/coder-$version_major-$rel_minor)"
+		fi
+
+		# Add row to table
+		result+="| $formatted_version_name | $formatted_date | $status | $patch_link |\n"
+	done
+
+	echo -e "$result"
+}
+
+# Check if the markdown comments exist in the file
+if ! grep -q "$CALENDAR_START_MARKER" "$DOCS_FILE" || ! grep -q "$CALENDAR_END_MARKER" "$DOCS_FILE"; then
+	echo "Error: Markdown comment anchors not found in $DOCS_FILE"
+	echo "Please add the following anchors around the release calendar table:"
+	echo "  $CALENDAR_START_MARKER"
+	echo "  $CALENDAR_END_MARKER"
+	exit 1
+fi
+
+# Generate the new calendar table content
+NEW_CALENDAR=$(generate_release_calendar)
+
+# Update the file while preserving the rest of the content
+awk -v start_marker="$CALENDAR_START_MARKER" \
+	-v end_marker="$CALENDAR_END_MARKER" \
+	-v new_calendar="$NEW_CALENDAR" \
+	'
+    BEGIN { found_start = 0; found_end = 0; print_line = 1; }
+    $0 ~ start_marker {
+        print;
+        print new_calendar;
+        found_start = 1;
+        print_line = 0;
+        next;
+    }
+    $0 ~ end_marker {
+        found_end = 1;
+        print_line = 1;
+        print;
+        next;
+    }
+    print_line || !found_start || found_end { print }
+    ' "$DOCS_FILE" >"${DOCS_FILE}.new"
+
+# Replace the original file with the updated version
+mv "${DOCS_FILE}.new" "$DOCS_FILE"
+
+# run make fmt/markdown
+make fmt/markdown
+
+echo "Successfully updated release calendar in $DOCS_FILE"