diff --git a/git-send-email.perl b/git-send-email.perl
index 8eb63b5a2f..3f66e1cdc2 100755
--- a/git-send-email.perl
+++ b/git-send-email.perl
@@ -1866,7 +1866,7 @@ sub apply_transfer_encoding {
 	$message = MIME::Base64::decode($message)
 		if ($from eq 'base64');
 
-	$to = ($message =~ /.{999,}/) ? 'quoted-printable' : '8bit'
+	$to = ($message =~ /(?:.{999,}|\r)/) ? 'quoted-printable' : '8bit'
 		if $to eq 'auto';
 
 	die __("cannot send message as 7bit")
diff --git a/t/t9001-send-email.sh b/t/t9001-send-email.sh
index ee1efcc59d..1e3ac3c384 100755
--- a/t/t9001-send-email.sh
+++ b/t/t9001-send-email.sh
@@ -481,6 +481,20 @@ test_expect_success $PREREQ 'long lines with auto encoding are quoted-printable'
 	grep "Content-Transfer-Encoding: quoted-printable" msgtxt1
 '
 
+test_expect_success $PREREQ 'carriage returns with auto encoding are quoted-printable' '
+	clean_fake_sendmail &&
+	cp $patches cr.patch &&
+	printf "this is a line\r\n" >>cr.patch &&
+	git send-email \
+		--from="Example <nobody@example.com>" \
+		--to=nobody@example.com \
+		--smtp-server="$(pwd)/fake.sendmail" \
+		--transfer-encoding=auto \
+		--no-validate \
+		cr.patch &&
+	grep "Content-Transfer-Encoding: quoted-printable" msgtxt1
+'
+
 for enc in auto quoted-printable base64
 do
 	test_expect_success $PREREQ "--validate passes with encoding $enc" '