parentFd, baseName, err := OpenParentDirectoryNoSymlinks(file.Path)
        if err != nil {
+               if os.IsNotExist(err) && s.req.DryRun {
+                       change.Created = true
+                       debugf("will create (parent missing)")
+                       *changed = true
+                       debugf("dry-run, skipping changes")
+                       s.resp.FileChanges = append(s.resp.FileChanges, change)
+                       return nil
+               }
                return err
        }
        defer unix.Close(parentFd)
 
                        nil,
                },
 
+               {
+                       "file: create, missing parent (dry-run)",
+                       safcm.MsgSyncReq{
+                               DryRun: true,
+                       },
+                       &safcm.File{
+                               Path:      "does-not-exist/file",
+                               Mode:      0644,
+                               Uid:       -1,
+                               Gid:       -1,
+                               Data:      []byte("content\n"),
+                               OrigGroup: "group",
+                       },
+                       nil,
+                       true,
+                       []ft.File{root},
+                       safcm.MsgSyncResp{
+                               FileChanges: []safcm.FileChange{
+                                       {
+                                               Path:    "does-not-exist/file",
+                                               Created: true,
+                                               New: safcm.FileChangeInfo{
+                                                       Mode:  0644,
+                                                       User:  user,
+                                                       Uid:   uid,
+                                                       Group: group,
+                                                       Gid:   gid,
+                                               },
+                                       },
+                               },
+                       },
+                       []string{
+                               `4: files: "does-not-exist/file" (group): will create (parent missing)`,
+                               `4: files: "does-not-exist/file" (group): dry-run, skipping changes`,
+                       },
+                       nil,
+               },
+
                {
                        "file: unchanged",
                        safcm.MsgSyncReq{},
                        nil,
                },
 
+               {
+                       "directory: create, missing parent (dry-run)",
+                       safcm.MsgSyncReq{
+                               DryRun: true,
+                       },
+                       &safcm.File{
+                               Path:      "does-not-exist/dir",
+                               Mode:      fs.ModeDir | 0755,
+                               Uid:       -1,
+                               Gid:       -1,
+                               OrigGroup: "group",
+                       },
+                       nil,
+                       true,
+                       []ft.File{root},
+                       safcm.MsgSyncResp{
+                               FileChanges: []safcm.FileChange{
+                                       {
+                                               Path:    "does-not-exist/dir",
+                                               Created: true,
+                                               New: safcm.FileChangeInfo{
+                                                       Mode:  fs.ModeDir | 0755,
+                                                       User:  user,
+                                                       Uid:   uid,
+                                                       Group: group,
+                                                       Gid:   gid,
+                                               },
+                                       },
+                               },
+                       },
+                       []string{
+                               `4: files: "does-not-exist/dir" (group): will create (parent missing)`,
+                               `4: files: "does-not-exist/dir" (group): dry-run, skipping changes`,
+                       },
+                       nil,
+               },
+
                {
                        "directory: unchanged",
                        safcm.MsgSyncReq{},