diff --git a/connect.c b/connect.c
index 170e39122..1f7b7694f 100644
--- a/connect.c
+++ b/connect.c
@@ -722,7 +722,7 @@ struct child_process *git_connect(int fd[2], const char *url,
 		conn->in = conn->out = -1;
 		if (protocol == PROTO_SSH) {
 			const char *ssh;
-			int putty;
+			int putty, tortoiseplink = 0;
 			char *ssh_host = hostandport;
 			const char *port = NULL;
 			get_host_and_port(&ssh_host, &port);
@@ -747,14 +747,26 @@ struct child_process *git_connect(int fd[2], const char *url,
 				conn->use_shell = 1;
 				putty = 0;
 			} else {
+				const char *base;
+				char *ssh_dup;
+
 				ssh = getenv("GIT_SSH");
 				if (!ssh)
 					ssh = "ssh";
-				putty = !!strcasestr(ssh, "plink");
+
+				ssh_dup = xstrdup(ssh);
+				base = basename(ssh_dup);
+
+				tortoiseplink = !strcasecmp(base, "tortoiseplink") ||
+					!strcasecmp(base, "tortoiseplink.exe");
+				putty = !strcasecmp(base, "plink") ||
+					!strcasecmp(base, "plink.exe") || tortoiseplink;
+
+				free(ssh_dup);
 			}
 
 			argv_array_push(&conn->args, ssh);
-			if (putty && !strcasestr(ssh, "tortoiseplink"))
+			if (tortoiseplink)
 				argv_array_push(&conn->args, "-batch");
 			if (port) {
 				/* P is for PuTTY, p is for OpenSSH */
diff --git a/t/t5601-clone.sh b/t/t5601-clone.sh
index 5efc17791..731c09c41 100755
--- a/t/t5601-clone.sh
+++ b/t/t5601-clone.sh
@@ -296,6 +296,12 @@ setup_ssh_wrapper () {
 	'
 }
 
+copy_ssh_wrapper_as () {
+	cp "$TRASH_DIRECTORY/ssh-wrapper" "$1" &&
+	GIT_SSH="$1" &&
+	export GIT_SSH
+}
+
 expect_ssh () {
 	test_when_finished '
 		(cd "$TRASH_DIRECTORY" && rm -f ssh-expect && >ssh-output)
@@ -335,6 +341,33 @@ test_expect_success 'bracketed hostnames are still ssh' '
 	expect_ssh "-p 123" myhost src
 '
 
+test_expect_success 'uplink is not treated as putty' '
+	copy_ssh_wrapper_as "$TRASH_DIRECTORY/uplink" &&
+	git clone "[myhost:123]:src" ssh-bracket-clone-uplink &&
+	expect_ssh "-p 123" myhost src
+'
+
+test_expect_success 'plink is treated specially (as putty)' '
+	copy_ssh_wrapper_as "$TRASH_DIRECTORY/plink" &&
+	git clone "[myhost:123]:src" ssh-bracket-clone-plink-0 &&
+	expect_ssh "-P 123" myhost src
+'
+
+test_expect_success 'plink.exe is treated specially (as putty)' '
+	copy_ssh_wrapper_as "$TRASH_DIRECTORY/plink.exe" &&
+	git clone "[myhost:123]:src" ssh-bracket-clone-plink-1 &&
+	expect_ssh "-P 123" myhost src
+'
+
+test_expect_success 'tortoiseplink is like putty, with extra arguments' '
+	copy_ssh_wrapper_as "$TRASH_DIRECTORY/tortoiseplink" &&
+	git clone "[myhost:123]:src" ssh-bracket-clone-plink-2 &&
+	expect_ssh "-batch -P 123" myhost src
+'
+
+# Reset the GIT_SSH environment variable for clone tests.
+setup_ssh_wrapper
+
 counter=0
 # $1 url
 # $2 none|host