diff --git a/builtin/worktree.c b/builtin/worktree.c
index 093b2cb032..5f62084334 100644
--- a/builtin/worktree.c
+++ b/builtin/worktree.c
@@ -638,6 +638,9 @@ static int first_valid_ref(const char *refname,
  *
  * - Checks whether any valid local branches exist.
  *
+ * - Emits a warning if there exist any valid branches but HEAD does not point
+ *   to a valid reference.
+ *
  * Returns 1 if any of the previous checks are true, otherwise returns 0.
  */
 static int can_use_local_refs(const struct add_opts *opts)
@@ -645,6 +648,23 @@ static int can_use_local_refs(const struct add_opts *opts)
 	if (head_ref(first_valid_ref, NULL)) {
 		return 1;
 	} else if (for_each_branch_ref(first_valid_ref, NULL)) {
+		if (!opts->quiet) {
+			struct strbuf path = STRBUF_INIT;
+			struct strbuf contents = STRBUF_INIT;
+
+			strbuf_add_real_path(&path, get_worktree_git_dir(NULL));
+			strbuf_addstr(&path, "/HEAD");
+			strbuf_read_file(&contents, path.buf, 64);
+			strbuf_stripspace(&contents, 0);
+			strbuf_strip_suffix(&contents, "\n");
+
+			warning(_("HEAD points to an invalid (or orphaned) reference.\n"
+				  "HEAD path: '%s'\n"
+				  "HEAD contents: '%s'"),
+				  path.buf, contents.buf);
+			strbuf_release(&path);
+			strbuf_release(&contents);
+		}
 		return 1;
 	}
 	return 0;
@@ -666,16 +686,12 @@ static int can_use_local_refs(const struct add_opts *opts)
 static int can_use_remote_refs(const struct add_opts *opts)
 {
 	if (!guess_remote) {
-		if (!opts->quiet)
-			fprintf_ln(stderr, WORKTREE_ADD_DWIM_ORPHAN_INFER_TEXT);
 		return 0;
 	} else if (for_each_remote_ref(first_valid_ref, NULL)) {
 		return 1;
 	} else if (!opts->force && remote_get(NULL)) {
 		die(_("No local or remote refs exist despite at least one remote\n"
 		      "present, stopping; use 'add -f' to overide or fetch a remote first"));
-	} else if (!opts->quiet) {
-		fprintf_ln(stderr, WORKTREE_ADD_DWIM_ORPHAN_INFER_TEXT);
 	}
 	return 0;
 }
@@ -828,8 +844,12 @@ static int add(int ac, const char **av, const char *prefix)
 		int n;
 		const char *s = worktree_basename(path, &n);
 		new_branch = xstrndup(s, n);
-	} else if (opts.orphan || opts.detach) {
+	} else if (opts.orphan) {
 		// No-op
+	} else if (opts.detach) {
+		// Check HEAD
+		if (!strcmp(branch, "HEAD"))
+			can_use_local_refs(&opts);
 	} else if (ac < 2 && new_branch) {
 		// DWIM: Infer --orphan when repo has no refs.
 		opts.orphan = dwim_orphan(&opts, !!opt_track, 0);
@@ -854,6 +874,10 @@ static int add(int ac, const char **av, const char *prefix)
 				branch = remote;
 			}
 		}
+
+		if (!strcmp(branch, "HEAD"))
+			can_use_local_refs(&opts);
+
 	}
 
 	if (!opts.orphan && !lookup_commit_reference_by_name(branch)) {
diff --git a/t/t2400-worktree-add.sh b/t/t2400-worktree-add.sh
index c7ca8df586..0ac468e69e 100755
--- a/t/t2400-worktree-add.sh
+++ b/t/t2400-worktree-add.sh
@@ -722,6 +722,7 @@ test_dwim_orphan () {
 	local use_quiet=0 &&
 	local remote=0 &&
 	local remote_ref=0 &&
+	local use_detach=0 &&
 	local use_new_branch=0 &&
 
 	local outcome="$1" &&
@@ -747,6 +748,10 @@ test_dwim_orphan () {
 		success=0 &&
 		outcome_text='"add" error inferred "--orphan" gives illegal opts combo'
 		;;
+	"warn_bad_head")
+		success=0 &&
+		outcome_text='"add" error, warn on bad HEAD, hint use orphan'
+		;;
 	*)
 		echo "test_dwim_orphan(): invalid outcome: '$outcome'" >&2 &&
 		return 1
@@ -818,7 +823,7 @@ test_dwim_orphan () {
 			context="$context, invalid (or orphan) HEAD"
 			;;
 
-		# Whether the code path is tested with the base add command or -b
+		# Whether the code path is tested with the base add command, -b, or --detach
 		"no_-b")
 			use_new_branch=0 &&
 			context="$context, no --branch"
@@ -827,6 +832,10 @@ test_dwim_orphan () {
 			use_new_branch=1 &&
 			context="$context, --branch"
 			;;
+		"detach")
+			use_detach=1 &&
+			context="$context, --detach"
+			;;
 
 		# Whether to check that all output is suppressed (except errors)
 		# or that the output is as expected
@@ -887,6 +896,9 @@ test_dwim_orphan () {
 	if [ $use_new_branch -eq 1 ]
 	then
 		args="$args -b foo"
+	elif [ $use_detach -eq 1 ]
+	then
+		args="$args --detach"
 	else
 		context="DWIM (no --branch), $context"
 	fi &&
@@ -1023,6 +1035,10 @@ do
 		test_dwim_orphan 'infer' $dwim_test_args -b no_local_ref remote no_remote_ref no_guess_remote
 		test_dwim_orphan 'infer' $dwim_test_args -b no_local_ref remote no_remote_ref guess_remote
 		test_dwim_orphan 'infer' $dwim_test_args -b no_local_ref remote remote_ref guess_remote
+
+		test_dwim_orphan 'warn_bad_head' $dwim_test_args no_-b local_ref bad_head
+		test_dwim_orphan 'warn_bad_head' $dwim_test_args -b local_ref bad_head
+		test_dwim_orphan 'warn_bad_head' $dwim_test_args detach local_ref bad_head
 	done
 
 	test_dwim_orphan 'fatal_orphan_bad_combo' $quiet_mode no_-b no_checkout