diff --git a/src/basic/hostname-util.c b/src/basic/hostname-util.c
index 9410dd05d23..ea49676ea30 100644
--- a/src/basic/hostname-util.c
+++ b/src/basic/hostname-util.c
@@ -132,7 +132,7 @@ char* hostname_cleanup(char *s) {
                         hyphen = false;
                 }
 
-        if (d > s && IN_SET(d[-1], '-', '.'))
+        while (d > s && IN_SET(d[-1], '-', '.'))
                 /* The dot can occur at most once, but we might have multiple
                  * hyphens, hence the loop */
                 d--;
diff --git a/src/test/test-hostname-util.c b/src/test/test-hostname-util.c
index 513c8edc9b8..d2b590197cf 100644
--- a/src/test/test-hostname-util.c
+++ b/src/test/test-hostname-util.c
@@ -85,6 +85,14 @@ TEST(hostname_cleanup) {
         ASSERT_STREQ(hostname_cleanup(s), "foo.bar");
         s = strdupa_safe("foo.bar..");
         ASSERT_STREQ(hostname_cleanup(s), "foo.bar");
+        s = strdupa_safe("foobar--");
+        ASSERT_STREQ(hostname_cleanup(s), "foobar");
+        s = strdupa_safe("foobar-.");
+        ASSERT_STREQ(hostname_cleanup(s), "foobar");
+        s = strdupa_safe("foobar.-");
+        ASSERT_STREQ(hostname_cleanup(s), "foobar");
+        s = strdupa_safe("foobar-.-");
+        ASSERT_STREQ(hostname_cleanup(s), "foobar");
         s = strdupa_safe("xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx");
         ASSERT_STREQ(hostname_cleanup(s), "xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx");
         s = strdupa_safe("xxxx........xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx");