diff --git a/Documentation/config/advice.txt b/Documentation/config/advice.txt
index c7ea70f2e2e9d2..cdaa6b9a71b151 100644
--- a/Documentation/config/advice.txt
+++ b/Documentation/config/advice.txt
@@ -56,6 +56,9 @@ advice.*::
 		Advice on how to set your identity configuration when
 		your information is guessed from the system username and
 		domain name.
+	nameTooLong::
+		Advice shown if a filepath operation is attempted where the
+		path was too long.
 	nestedTag::
 		Advice shown if a user attempts to recursively tag a tag object.
 	pushAlreadyExists::
diff --git a/advice.c b/advice.c
index 6e9098ff08935a..b6a41df95d21d0 100644
--- a/advice.c
+++ b/advice.c
@@ -57,6 +57,7 @@ static struct {
 	[ADVICE_GRAFT_FILE_DEPRECATED]			= { "graftFileDeprecated" },
 	[ADVICE_IGNORED_HOOK]				= { "ignoredHook" },
 	[ADVICE_IMPLICIT_IDENTITY]			= { "implicitIdentity" },
+	[ADVICE_NAME_TOO_LONG]				= { "nameTooLong" },
 	[ADVICE_NESTED_TAG]				= { "nestedTag" },
 	[ADVICE_OBJECT_NAME_WARNING]			= { "objectNameWarning" },
 	[ADVICE_PUSH_ALREADY_EXISTS]			= { "pushAlreadyExists" },
diff --git a/advice.h b/advice.h
index 9d4f49ae38bcfe..532ad2edb50cce 100644
--- a/advice.h
+++ b/advice.h
@@ -25,6 +25,7 @@ enum advice_type {
 	ADVICE_GRAFT_FILE_DEPRECATED,
 	ADVICE_IGNORED_HOOK,
 	ADVICE_IMPLICIT_IDENTITY,
+	ADVICE_NAME_TOO_LONG,
 	ADVICE_NESTED_TAG,
 	ADVICE_OBJECT_NAME_WARNING,
 	ADVICE_PUSH_ALREADY_EXISTS,
diff --git a/builtin/clean.c b/builtin/clean.c
index b282bb4b2b47d1..c9fd2e2f3c97dd 100644
--- a/builtin/clean.c
+++ b/builtin/clean.c
@@ -24,6 +24,7 @@
 #include "pathspec.h"
 #include "help.h"
 #include "prompt.h"
+#include "advice.h"
 
 static int force = -1; /* unset */
 static int interactive;
@@ -219,6 +220,9 @@ static int remove_dirs(struct strbuf *path, const char *prefix, int force_flag,
 			quote_path(path->buf, prefix, &quoted, 0);
 			errno = saved_errno;
 			warning_errno(_(msg_warn_remove_failed), quoted.buf);
+			if (saved_errno == ENAMETOOLONG) {
+				advise_if_enabled(ADVICE_NAME_TOO_LONG, _("Setting `core.longPaths` may allow the deletion to succeed."));
+			}
 			*dir_gone = 0;
 		}
 		ret = res;
@@ -254,6 +258,9 @@ static int remove_dirs(struct strbuf *path, const char *prefix, int force_flag,
 				quote_path(path->buf, prefix, &quoted, 0);
 				errno = saved_errno;
 				warning_errno(_(msg_warn_remove_failed), quoted.buf);
+				if (saved_errno == ENAMETOOLONG) {
+					advise_if_enabled(ADVICE_NAME_TOO_LONG, _("Setting `core.longPaths` may allow the deletion to succeed."));
+				}
 				*dir_gone = 0;
 				ret = 1;
 			}
@@ -297,6 +304,9 @@ static int remove_dirs(struct strbuf *path, const char *prefix, int force_flag,
 				quote_path(path->buf, prefix, &quoted, 0);
 				errno = saved_errno;
 				warning_errno(_(msg_warn_remove_failed), quoted.buf);
+				if (saved_errno == ENAMETOOLONG) {
+					advise_if_enabled(ADVICE_NAME_TOO_LONG, _("Setting `core.longPaths` may allow the deletion to succeed."));
+				}
 				*dir_gone = 0;
 				ret = 1;
 			}
@@ -1116,6 +1126,9 @@ int cmd_clean(int argc, const char **argv, const char *prefix)
 				qname = quote_path(item->string, NULL, &buf, 0);
 				errno = saved_errno;
 				warning_errno(_(msg_warn_remove_failed), qname);
+				if (saved_errno == ENAMETOOLONG) {
+					advise_if_enabled(ADVICE_NAME_TOO_LONG, _("Setting `core.longPaths` may allow the deletion to succeed."));
+				}
 				errors++;
 			} else if (!quiet) {
 				qname = quote_path(item->string, NULL, &buf, 0);