diff --git a/src/partition/repart.c b/src/partition/repart.c
index 3e88d38205..3b31109952 100644
--- a/src/partition/repart.c
+++ b/src/partition/repart.c
@@ -2801,15 +2801,6 @@ static int do_copy_files(Partition *p, const char *fs) {
 
         STRV_FOREACH_PAIR(source, target, p->copy_files) {
                 _cleanup_close_ int sfd = -1, pfd = -1, tfd = -1;
-                _cleanup_free_ char *dn = NULL, *fn = NULL;
-
-                r = path_extract_directory(*target, &dn);
-                if (r < 0)
-                        return log_error_errno(r, "Failed to extract directory from '%s': %m", *target);
-
-                r = path_extract_filename(*target, &fn);
-                if (r < 0)
-                        return log_error_errno(r, "Failed to extract filename from '%s': %m", *target);
 
                 sfd = chase_symlinks_and_open(*source, arg_root, CHASE_PREFIX_ROOT|CHASE_WARN, O_CLOEXEC|O_NOCTTY, NULL);
                 if (sfd < 0)
@@ -2823,9 +2814,19 @@ static int do_copy_files(Partition *p, const char *fs) {
                         /* We are looking at a directory */
                         tfd = chase_symlinks_and_open(*target, fs, CHASE_PREFIX_ROOT|CHASE_WARN, O_RDONLY|O_DIRECTORY|O_CLOEXEC, NULL);
                         if (tfd < 0) {
+                                _cleanup_free_ char *dn = NULL, *fn = NULL;
+
                                 if (tfd != -ENOENT)
                                         return log_error_errno(tfd, "Failed to open target directory '%s': %m", *target);
 
+                                r = path_extract_filename(*target, &fn);
+                                if (r < 0)
+                                        return log_error_errno(r, "Failed to extract filename from '%s': %m", *target);
+
+                                r = path_extract_directory(*target, &dn);
+                                if (r < 0)
+                                        return log_error_errno(r, "Failed to extract directory from '%s': %m", *target);
+
                                 r = mkdir_p_root(fs, dn, UID_INVALID, GID_INVALID, 0755);
                                 if (r < 0)
                                         return log_error_errno(r, "Failed to create parent directory '%s': %m", dn);
@@ -2846,10 +2847,23 @@ static int do_copy_files(Partition *p, const char *fs) {
                                                 UID_INVALID, GID_INVALID,
                                                 COPY_REFLINK|COPY_MERGE|COPY_REPLACE|COPY_SIGINT|COPY_HARDLINKS);
                         if (r < 0)
-                                return log_error_errno(r, "Failed to copy %s%s to %s: %m", strempty(arg_root), *source, *target);
+                                return log_error_errno(r, "Failed to copy '%s' to '%s%s': %m", *source, strempty(arg_root), *target);
                 } else {
+                        _cleanup_free_ char *dn = NULL, *fn = NULL;
+
                         /* We are looking at a regular file */
 
+                        r = path_extract_filename(*target, &fn);
+                        if (r == -EADDRNOTAVAIL || r == O_DIRECTORY)
+                                return log_error_errno(SYNTHETIC_ERRNO(EISDIR),
+                                                       "Target path '%s' refers to a directory, but source path '%s' refers to regular file, can't copy.", *target, *source);
+                        if (r < 0)
+                                return log_error_errno(r, "Failed to extract filename from '%s': %m", *target);
+
+                        r = path_extract_directory(*target, &dn);
+                        if (r < 0)
+                                return log_error_errno(r, "Failed to extract directory from '%s': %m", *target);
+
                         r = mkdir_p_root(fs, dn, UID_INVALID, GID_INVALID, 0755);
                         if (r < 0)
                                 return log_error_errno(r, "Failed to create parent directory: %m");
@@ -2858,13 +2872,13 @@ static int do_copy_files(Partition *p, const char *fs) {
                         if (pfd < 0)
                                 return log_error_errno(pfd, "Failed to open parent directory of target: %m");
 
-                        tfd = openat(pfd, basename(*target), O_CREAT|O_EXCL|O_WRONLY|O_CLOEXEC, 0700);
+                        tfd = openat(pfd, fn, O_CREAT|O_EXCL|O_WRONLY|O_CLOEXEC, 0700);
                         if (tfd < 0)
                                 return log_error_errno(errno, "Failed to create target file '%s': %m", *target);
 
                         r = copy_bytes(sfd, tfd, UINT64_MAX, COPY_REFLINK|COPY_SIGINT);
                         if (r < 0)
-                                return log_error_errno(r, "Failed to copy '%s%s' to '%s': %m", strempty(arg_root), *source, *target);
+                                return log_error_errno(r, "Failed to copy '%s' to '%s%s': %m", *source, strempty(arg_root), *target);
 
                         (void) copy_xattr(sfd, tfd);
                         (void) copy_access(sfd, tfd);