diff --git a/http.c b/http.c
index 5bc2ad8b873a77..c3182f422a1063 100644
--- a/http.c
+++ b/http.c
@@ -139,6 +139,7 @@ static unsigned long empty_auth_useless =
 	CURLAUTH_BASIC
 	| CURLAUTH_DIGEST_IE
 	| CURLAUTH_DIGEST;
+static int empty_auth_try_negotiate;
 
 static struct curl_slist *pragma_header;
 static struct string_list extra_http_headers = STRING_LIST_INIT_DUP;
@@ -704,6 +705,22 @@ static void init_curl_http_auth(CURL *result)
 	}
 }
 
+void http_reauth_prepare(int all_capabilities)
+{
+	/*
+	 * If we deferred stripping Negotiate to give empty auth a
+	 * chance (auto mode), skip credential_fill on this retry so
+	 * that init_curl_http_auth() sends empty credentials and
+	 * libcurl can attempt Negotiate with the system ticket cache.
+	 */
+	if (empty_auth_try_negotiate &&
+	    !http_auth.password && !http_auth.credential &&
+	    (http_auth_methods & CURLAUTH_GSSNEGOTIATE))
+		return;
+
+	credential_fill(the_repository, &http_auth, all_capabilities);
+}
+
 /* *var must be free-able */
 static void var_override(char **var, char *value)
 {
@@ -1954,7 +1971,18 @@ static int handle_curl_result(struct slot_results *results)
 			}
 			return HTTP_NOAUTH;
 		} else {
-			http_auth_methods &= ~CURLAUTH_GSSNEGOTIATE;
+			if (curl_empty_auth == -1 &&
+			    !empty_auth_try_negotiate &&
+			    (results->auth_avail & CURLAUTH_GSSNEGOTIATE)) {
+				/*
+				 * In auto mode, give Negotiate a chance via
+				 * empty auth before stripping it. If it fails,
+				 * we will strip it on the next 401.
+				 */
+				empty_auth_try_negotiate = 1;
+			} else {
+				http_auth_methods &= ~CURLAUTH_GSSNEGOTIATE;
+			}
 			if (results->auth_avail) {
 				http_auth_methods &= results->auth_avail;
 				http_auth_methods_restricted = 1;
@@ -2462,7 +2490,7 @@ static int http_request_recoverable(const char *url,
 				sleep(retry_delay);
 			}
 		} else if (ret == HTTP_REAUTH) {
-			credential_fill(the_repository, &http_auth, 1);
+			http_reauth_prepare(1);
 		}
 
 		/*
diff --git a/http.h b/http.h
index f9ee888c3ed67e..729c51904d39ad 100644
--- a/http.h
+++ b/http.h
@@ -76,6 +76,12 @@ extern int http_is_verbose;
 extern ssize_t http_post_buffer;
 extern struct credential http_auth;
 
+/**
+ * Prepare for an HTTP re-authentication retry. This fills credentials
+ * via credential_fill() so the next request can include them.
+ */
+void http_reauth_prepare(int all_capabilities);
+
 extern char curl_errorstr[CURL_ERROR_SIZE];
 
 enum http_follow_config {
diff --git a/remote-curl.c b/remote-curl.c
index aba60d571282d3..affdb880f7b3bf 100644
--- a/remote-curl.c
+++ b/remote-curl.c
@@ -946,7 +946,7 @@ static int post_rpc(struct rpc_state *rpc, int stateless_connect, int flush_rece
 		do {
 			err = probe_rpc(rpc, &results);
 			if (err == HTTP_REAUTH)
-				credential_fill(the_repository, &http_auth, 0);
+				http_reauth_prepare(0);
 		} while (err == HTTP_REAUTH);
 		if (err != HTTP_OK)
 			return -1;
@@ -1068,7 +1068,7 @@ static int post_rpc(struct rpc_state *rpc, int stateless_connect, int flush_rece
 	rpc->any_written = 0;
 	err = run_slot(slot, NULL);
 	if (err == HTTP_REAUTH && !large_request) {
-		credential_fill(the_repository, &http_auth, 0);
+		http_reauth_prepare(0);
 		curl_slist_free_all(headers);
 		goto retry;
 	}
diff --git a/t/t5563-simple-http-auth.sh b/t/t5563-simple-http-auth.sh
index 35e6f4b397da7c..911c716aaff2f4 100755
--- a/t/t5563-simple-http-auth.sh
+++ b/t/t5563-simple-http-auth.sh
@@ -748,4 +748,78 @@ test_expect_success NTLM 'access using NTLM auth' '
 	git ls-remote "$HTTPD_URL/ntlm_auth/repo.git"
 '
 
+test_lazy_prereq SPNEGO 'curl --version | grep -qi "SPNEGO\|GSS-API\|Kerberos\|negotiate"'
+
+test_expect_success SPNEGO 'http.emptyAuth=auto attempts Negotiate before credential_fill' '
+	test_when_finished "per_test_cleanup" &&
+
+	set_credential_reply get <<-EOF &&
+	username=alice
+	password=secret-passwd
+	EOF
+
+	# Basic base64(alice:secret-passwd)
+	cat >"$HTTPD_ROOT_PATH/custom-auth.valid" <<-EOF &&
+	id=1 creds=Basic YWxpY2U6c2VjcmV0LXBhc3N3ZA==
+	EOF
+
+	cat >"$HTTPD_ROOT_PATH/custom-auth.challenge" <<-EOF &&
+	id=1 status=200
+	id=default response=WWW-Authenticate: Negotiate
+	id=default response=WWW-Authenticate: Basic realm="example.com"
+	EOF
+
+	test_config_global credential.helper test-helper &&
+	GIT_TRACE_CURL="$TRASH_DIRECTORY/trace-auto" \
+		git -c http.emptyAuth=auto \
+		ls-remote "$HTTPD_URL/custom_auth/repo.git" &&
+
+	# In auto mode with a Negotiate+Basic server, there should be
+	# three 401 responses: (1) initial no-auth request, (2) empty-auth
+	# retry where Negotiate fails (no Kerberos ticket), (3) libcurl
+	# internal Negotiate retry. The fourth attempt uses Basic
+	# credentials from credential_fill and succeeds.
+	grep "HTTP/[0-9.]* 401" "$TRASH_DIRECTORY/trace-auto" >actual_401s &&
+	test_line_count = 3 actual_401s &&
+
+	expect_credential_query get <<-EOF
+	capability[]=authtype
+	capability[]=state
+	protocol=http
+	host=$HTTPD_DEST
+	wwwauth[]=Negotiate
+	wwwauth[]=Basic realm="example.com"
+	EOF
+'
+
+test_expect_success SPNEGO 'http.emptyAuth=false skips Negotiate' '
+	test_when_finished "per_test_cleanup" &&
+
+	set_credential_reply get <<-EOF &&
+	username=alice
+	password=secret-passwd
+	EOF
+
+	# Basic base64(alice:secret-passwd)
+	cat >"$HTTPD_ROOT_PATH/custom-auth.valid" <<-EOF &&
+	id=1 creds=Basic YWxpY2U6c2VjcmV0LXBhc3N3ZA==
+	EOF
+
+	cat >"$HTTPD_ROOT_PATH/custom-auth.challenge" <<-EOF &&
+	id=1 status=200
+	id=default response=WWW-Authenticate: Negotiate
+	id=default response=WWW-Authenticate: Basic realm="example.com"
+	EOF
+
+	test_config_global credential.helper test-helper &&
+	GIT_TRACE_CURL="$TRASH_DIRECTORY/trace-false" \
+		git -c http.emptyAuth=false \
+		ls-remote "$HTTPD_URL/custom_auth/repo.git" &&
+
+	# With emptyAuth=false, Negotiate is stripped immediately and
+	# credential_fill is called right away. Only one 401 response.
+	grep "HTTP/[0-9.]* 401" "$TRASH_DIRECTORY/trace-false" >actual_401s &&
+	test_line_count = 1 actual_401s
+'
+
 test_done