diff --git a/src/shared/discover-image.c b/src/shared/discover-image.c
index 07d0ff128f..99c5365a89 100644
--- a/src/shared/discover-image.c
+++ b/src/shared/discover-image.c
@@ -618,7 +618,7 @@ static int image_make(
                 (*ret)->foreign_uid_owned = uid_is_foreign(st->st_uid);
                 return 0;
 
-        } else if (S_ISREG(st->st_mode) && endswith(path, ".raw")) {
+        } else if (S_ISREG(st->st_mode) && (endswith(path, ".raw") || pretty)) {
                 usec_t crtime = 0;
 
                 /* It's a RAW disk image */
diff --git a/test/units/TEST-13-NSPAWN.machined.sh b/test/units/TEST-13-NSPAWN.machined.sh
index 6b07137ef8..e0035c4677 100755
--- a/test/units/TEST-13-NSPAWN.machined.sh
+++ b/test/units/TEST-13-NSPAWN.machined.sh
@@ -229,6 +229,16 @@ machinectl import-fs /var/tmp/container.dir container-dir
 machinectl start container-dir
 rm -fr /var/tmp/container.dir
 
+# Check if machinectl can properly work with symlinks to raw images
+touch /var/lib/machines/linked.squashfs
+ln -svrf /var/lib/machines/linked.squashfs /var/lib/machines/linked.raw
+ls -la /var/lib/machines/
+machinectl list-images | tee /tmp/out.log
+grep -E "linked\s+raw" /tmp/out.log
+(! grep -E "squashfs" /tmp/out.log)
+[[ "$(machinectl show-image --property=Type --value linked)" == "raw" ]]
+rm -f /var/lib/machines/linked.{squashfs,raw} /tmp/out.log
+
 timeout 30 bash -c "until machinectl clean --all; do sleep .5; done"
 
 NSPAWN_FRAGMENT="machinectl-test-$RANDOM.nspawn"