diff --git a/.github/workflows/changelog-generator.yml b/.github/workflows/changelog-generator.yml
new file mode 100644
index 00000000..c47f2d53
--- /dev/null
+++ b/.github/workflows/changelog-generator.yml
@@ -0,0 +1,139 @@
+name: Generate Changelog
+
+on:
+  milestone:
+    types: [closed]
+  workflow_dispatch: 
+    inputs:
+      milestone:
+        description: 'Milestone number or title to generate changelog for'
+        required: true
+        type: string
+      dry_run:
+        description: 'Preview changelog without committing'
+        required: false
+        type: boolean
+        default: false
+
+permissions:
+  contents: write
+  pull-requests: read
+
+jobs:
+  generate-changelog:
+    name: Generate WordPress readme.txt Changelog
+    runs-on: ubuntu-latest
+    
+    steps: 
+      - name: Checkout repository
+        uses: actions/checkout@v4
+        with:
+          fetch-depth: 0
+          token: ${{ secrets.GITHUB_TOKEN }}
+      
+      - name: Setup PHP
+        uses: shivammathur/setup-php@v2
+        with:
+          php-version: '8.4'
+          tools: composer:v2
+      
+      - name: Install dependencies
+        run: composer install --no-progress --prefer-dist --no-interaction
+      
+      - name: Get milestone information
+        id: milestone
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+          MILESTONE_INPUT: ${{ github.event.inputs.milestone }}
+          EVENT_MILESTONE: ${{ github.event.milestone.number }}
+        run: |
+          if [ -n "$MILESTONE_INPUT" ]; then
+            MILESTONE="$MILESTONE_INPUT"
+          else
+            MILESTONE="$EVENT_MILESTONE"
+          fi
+          
+          echo "milestone=$MILESTONE" >> $GITHUB_OUTPUT
+          
+          # Fetch milestone details
+          MILESTONE_DATA=$(gh api "repos/${{ github.repository }}/milestones" \
+            --jq ". [] | select(.number == $MILESTONE or .title == \"$MILESTONE\")")
+          
+          MILESTONE_TITLE=$(echo "$MILESTONE_DATA" | jq -r '.title')
+          MILESTONE_NUMBER=$(echo "$MILESTONE_DATA" | jq -r '.number')
+          DUE_DATE=$(echo "$MILESTONE_DATA" | jq -r '.due_on // empty')
+          
+          echo "title=$MILESTONE_TITLE" >> $GITHUB_OUTPUT
+          echo "number=$MILESTONE_NUMBER" >> $GITHUB_OUTPUT
+          
+          if [ -n "$DUE_DATE" ]; then
+            FORMATTED_DATE=$(date -d "$DUE_DATE" "+%d %b %Y")
+            echo "date=$FORMATTED_DATE" >> $GITHUB_OUTPUT
+          else
+            FORMATTED_DATE=$(date "+%d %b %Y")
+            echo "date=$FORMATTED_DATE" >> $GITHUB_OUTPUT
+          fi
+      
+      - name:  Fetch PRs from milestone
+        id: prs
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+          MILESTONE_NUMBER: ${{ steps.milestone.outputs.number }}
+        run: |
+          # Fetch all merged PRs in this milestone
+          gh pr list \
+            --repo "${{ github.repository }}" \
+            --state merged \
+            --milestone "$MILESTONE_NUMBER" \
+            --limit 1000 \
+            --json number,title,labels,author,mergedAt \
+            > prs.json
+          
+          echo "Found $(jq length prs.json) merged PRs in milestone"
+      
+      - name: Generate changelog entry
+        id: changelog
+        env:
+          MILESTONE_TITLE: ${{ steps.milestone.outputs.title }}
+          RELEASE_DATE: ${{ steps.milestone.outputs.date }}
+        run: |
+          php bin/generate-changelog.php \
+            --milestone-title "$MILESTONE_TITLE" \
+            --release-date "$RELEASE_DATE" \
+            --prs-file prs.json \
+            --output changelog-entry.txt
+          
+          echo "Generated changelog entry:"
+          cat changelog-entry.txt
+      
+      - name: Update readme.txt
+        if: github.event.inputs.dry_run != 'true'
+        run: |
+          php bin/update-readme-changelog.php \
+            --readme readme.txt \
+            --changelog-entry changelog-entry.txt \
+            --output readme.txt
+      
+      - name: Commit changes
+        if: github.event.inputs.dry_run != 'true'
+        env:
+          MILESTONE_TITLE: ${{ steps.milestone.outputs.title }}
+        run: |
+          git config user.name "github-actions[bot]"
+          git config user.email "github-actions[bot]@users.noreply.github.com"
+          
+          git add readme.txt
+          
+          if git diff --staged --quiet; then
+            echo "No changes to commit"
+          else
+            git commit -m "Update changelog for $MILESTONE_TITLE"
+            git push origin trunk
+          fi
+      
+      - name: Display changelog preview
+        if: github.event.inputs.dry_run == 'true'
+        run: |
+          echo "# Changelog Preview (Dry Run)"
+          echo ""
+          cat changelog-entry.txt
diff --git a/bin/generate-changelog.php b/bin/generate-changelog.php
new file mode 100644
index 00000000..9ac6f973
--- /dev/null
+++ b/bin/generate-changelog.php
@@ -0,0 +1,93 @@
+<?php
+/**
+ * Generate changelog entry from milestone PRs
+ * 
+ * Usage: php bin/generate-changelog. php --milestone-title "6.8.1" --release-date "15 Jan 2026" --prs-file prs. json --output changelog-entry.txt
+ */
+
+$options = getopt('', [
+    'milestone-title:',
+    'release-date:',
+    'prs-file:',
+    'output: ',
+]);
+
+$milestone_title = $options['milestone-title'] ?? '';
+$release_date = $options['release-date'] ?? date('d M Y');
+$prs_file = $options['prs-file'] ??  '';
+$output_file = $options['output'] ??  'php://stdout';
+
+if (empty($prs_file) || ! file_exists($prs_file)) {
+    fwrite(STDERR, "Error: PRs file not found\n");
+    exit(1);
+}
+
+$prs = json_decode(file_get_contents($prs_file), true);
+
+if ($prs === null) {
+    fwrite(STDERR, "Error: Invalid JSON in PRs file\n");
+    exit(1);
+}
+
+// Categorize PRs by label
+$categorized = [
+    'Features' => [],
+    'Enhancements' => [],
+    'Fixes' => [],
+    'Documentation' => [],
+    'Project Management' => [],
+    'Other' => [],
+];
+
+$label_mapping = [
+    '[Type] Feature' => 'Features',
+    '[Type] Enhancement' => 'Enhancements',
+    '[Type] Bug' => 'Fixes',
+    'documentation' => 'Documentation',
+    '[Type] Project Management' => 'Project Management',
+];
+
+foreach ($prs as $pr) {
+    $category = 'Other';
+    
+    foreach ($pr['labels'] as $label) {
+        $label_name = $label['name'];
+        if (isset($label_mapping[$label_name])) {
+            $category = $label_mapping[$label_name];
+            break;
+        }
+    }
+    
+    $categorized[$category][] = $pr;
+}
+
+// Generate changelog entry
+$changelog = "= {$milestone_title} =\n";
+$changelog .= "*Release Date {$release_date}*\n\n";
+
+foreach ($categorized as $category => $items) {
+    if (empty($items)) {
+        continue;
+    }
+    
+    $changelog .= "*{$category}*\n\n";
+    
+    foreach ($items as $pr) {
+        $title = $pr['title'];
+        // Remove common prefixes
+        $title = preg_replace('/^(Fix|Add|Update|Remove|Improve|Create|Delete|Refactor):\s*/i', '', $title);
+        $title = ucfirst($title);
+        
+        $changelog .= "- {$title}.\n";
+    }
+    
+    $changelog .= "\n";
+}
+
+// Write output
+if ($output_file === 'php://stdout') {
+    echo $changelog;
+} else {
+    file_put_contents($output_file, $changelog);
+    fwrite(STDERR, "Changelog entry written to {$output_file}\n");
+}
diff --git a/bin/update-readme-changelog.php b/bin/update-readme-changelog.php
new file mode 100644
index 00000000..21dbfaf5
--- /dev/null
+++ b/bin/update-readme-changelog.php
@@ -0,0 +1,50 @@
+<? php
+/**
+ * Update readme.txt with new changelog entry
+ * 
+ * Usage: php bin/update-readme-changelog.php --readme readme.txt --changelog-entry changelog-entry.txt --output readme.txt
+ */
+
+$options = getopt('', [
+    'readme:',
+    'changelog-entry:',
+    'output:',
+]);
+
+$readme_file = $options['readme'] ?? 'readme.txt';
+$changelog_entry_file = $options['changelog-entry'] ?? '';
+$output_file = $options['output'] ?? 'readme. txt';
+
+if (! file_exists($readme_file)) {
+    fwrite(STDERR, "Error: readme. txt not found at {$readme_file}\n");
+    exit(1);
+}
+
+if (!file_exists($changelog_entry_file)) {
+    fwrite(STDERR, "Error: changelog entry file not found at {$changelog_entry_file}\n");
+    exit(1);
+}
+
+$readme_content = file_get_contents($readme_file);
+$changelog_entry = file_get_contents($changelog_entry_file);
+
+// Find the changelog section
+$pattern = '/(== Changelog ==\s*\n\n)/';
+
+if (preg_match($pattern, $readme_content, $matches, PREG_OFFSET_CAPTURE)) {
+    $insert_position = $matches[0][1] + strlen($matches[0][0]);
+    
+    // Insert new changelog entry
+    $updated_content = substr_replace(
+        $readme_content,
+        $changelog_entry .  "\n",
+        $insert_position,
+        0
+    );
+    
+    file_put_contents($output_file, $updated_content);
+    echo "Successfully updated {$output_file}\n";
+} else {
+    fwrite(STDERR, "Error: Could not find Changelog section in readme.txt\n");
+    exit(1);
+}
diff --git a/composer.json b/composer.json
index 198be53f..9507b90b 100644
--- a/composer.json
+++ b/composer.json
@@ -66,6 +66,7 @@
 		"docs:lint": "npm run lint:md",
 		"docs:manifest": "php docs/bin/generate-manifest.php",
 		"docs:parse": "php docs/bin/generate-parsed-md.php --output=${DOCS_OUTPUT_DIR:-docs/code-reference}",
+		"changelog:generate": "php bin/generate-changelog.php"
 		"format": [
 			"@format:php",
 			"@format:packages"