diff --git a/tests/playground-ci/scripts/run-docs-agent.sh b/tests/playground-ci/scripts/run-docs-agent.sh
index 39333b9..53de4f7 100755
--- a/tests/playground-ci/scripts/run-docs-agent.sh
+++ b/tests/playground-ci/scripts/run-docs-agent.sh
@@ -4,6 +4,7 @@ set -euo pipefail
 SCRIPT_DIR="$(cd "$(dirname "${BASH_SOURCE[0]}")" && pwd)"
 REPO_ROOT="$(cd "$SCRIPT_DIR/../../.." && pwd)"
 COMPONENT_PATH="$REPO_ROOT/tests/playground-ci/component"
+DOCS_LINK_VALIDATOR="$SCRIPT_DIR/validate-docs-links.php"
 
 EXTENSION_PATH="${HOMEBOY_EXTENSION_PATH:-/Users/chubes/Developer/homeboy-extensions/wordpress}"
 AGENTS_API_PATH="${AGENTS_API_PATH:-$REPO_ROOT}"
@@ -276,6 +277,16 @@ if [ -n "${GITHUB_OUTPUT:-}" ]; then
     } >> "$GITHUB_OUTPUT"
 fi
 
+if [ "$job_status" = "completed" ] && [ "$success_status" = "pr_opened" ] && [[ "$DOCS_AGENT_FLOW_SLUG" == *-bootstrap-flow ]]; then
+    if [ ! -f "$DOCS_LINK_VALIDATOR" ]; then
+        echo "ERROR: Docs link validator missing at $DOCS_LINK_VALIDATOR" >&2
+        exit 1
+    fi
+
+    git -C "$AGENTS_API_PATH" fetch origin "$DOCS_AGENT_BRANCH"
+    php "$DOCS_LINK_VALIDATOR" "$AGENTS_API_PATH" FETCH_HEAD
+fi
+
 if [ "$job_status" = "completed" ] && { [ "$success_status" = "pr_opened" ] || [ "$success_status" = "no_changes" ]; }; then
     echo "Docs Agent maintenance PASSED - $success_status"
     exit 0
diff --git a/tests/playground-ci/scripts/validate-docs-links.php b/tests/playground-ci/scripts/validate-docs-links.php
new file mode 100644
index 0000000..9feee25
--- /dev/null
+++ b/tests/playground-ci/scripts/validate-docs-links.php
@@ -0,0 +1,105 @@
+<?php
+/**
+ * Validate relative Markdown links for a generated docs branch.
+ *
+ * Usage: php tests/playground-ci/scripts/validate-docs-links.php <repo-path> <git-ref>
+ */
+
+declare( strict_types=1 );
+
+$repo = $argv[1] ?? '';
+$ref  = $argv[2] ?? '';
+
+if ( '' === $repo || '' === $ref ) {
+	fwrite( STDERR, "Usage: php validate-docs-links.php <repo-path> <git-ref>\n" );
+	exit( 2 );
+}
+
+$run_git = static function ( array $args ) use ( $repo ): string {
+	$command = 'git -C ' . escapeshellarg( $repo );
+	foreach ( $args as $arg ) {
+		$command .= ' ' . escapeshellarg( (string) $arg );
+	}
+
+	$output = array();
+	$status = 0;
+	exec( $command, $output, $status );
+	if ( 0 !== $status ) {
+		throw new RuntimeException( "Git command failed: {$command}" );
+	}
+
+	return implode( "\n", $output );
+};
+
+$normalize_path = static function ( string $path ): string {
+	$parts = array();
+	foreach ( explode( '/', str_replace( '\\', '/', $path ) ) as $part ) {
+		if ( '' === $part || '.' === $part ) {
+			continue;
+		}
+		if ( '..' === $part ) {
+			array_pop( $parts );
+			continue;
+		}
+		$parts[] = $part;
+	}
+	return implode( '/', $parts );
+};
+
+$tree_output = $run_git( array( 'ls-tree', '-r', '--name-only', $ref ) );
+$all_files   = array_filter( explode( "\n", $tree_output ) );
+$file_set    = array_fill_keys( $all_files, true );
+$markdown_files = array_values(
+	array_filter(
+		$all_files,
+		static fn( string $file ): bool => ( 'README.md' === $file || str_starts_with( $file, 'docs/' ) ) && str_ends_with( strtolower( $file ), '.md' )
+	)
+);
+
+$missing = array();
+foreach ( $markdown_files as $file ) {
+	$content = $run_git( array( 'show', $ref . ':' . $file ) );
+	if ( ! preg_match_all( '/(?<!!)\[[^\]]*\]\(([^)\s]+)(?:\s+"[^"]*")?\)/', $content, $matches ) ) {
+		continue;
+	}
+
+	$base_dir = dirname( $file );
+	$base_dir = '.' === $base_dir ? '' : $base_dir;
+	foreach ( $matches[1] as $target ) {
+		$target = trim( html_entity_decode( $target, ENT_QUOTES | ENT_HTML5 ) );
+		if ( '' === $target || str_starts_with( $target, '#' ) || preg_match( '#^[a-z][a-z0-9+.-]*:#i', $target ) || str_starts_with( $target, '/' ) ) {
+			continue;
+		}
+
+		$target = preg_replace( '/[?#].*$/', '', $target );
+		$target = rawurldecode( $target );
+		$resolved = $normalize_path( ( '' === $base_dir ? '' : $base_dir . '/' ) . $target );
+		$candidates = array( $resolved );
+		if ( ! str_ends_with( strtolower( $resolved ), '.md' ) ) {
+			$candidates[] = $resolved . '.md';
+			$candidates[] = rtrim( $resolved, '/' ) . '/README.md';
+		}
+
+		$exists = false;
+		foreach ( $candidates as $candidate ) {
+			if ( isset( $file_set[ $candidate ] ) ) {
+				$exists = true;
+				break;
+			}
+		}
+
+		if ( ! $exists ) {
+			$missing[] = "{$file} -> {$target}";
+		}
+	}
+}
+
+if ( ! empty( $missing ) ) {
+	fwrite( STDERR, "Broken relative Markdown links found:\n" );
+	foreach ( $missing as $link ) {
+		fwrite( STDERR, "- {$link}\n" );
+	}
+	exit( 1 );
+}
+
+fwrite( STDOUT, "Docs Markdown link validation passed.\n" );