diff --git a/pkgs/clan-cli/clan_cli/ssh/upload.py b/pkgs/clan-cli/clan_cli/ssh/upload.py
index 08e5660b9..207ec49b2 100644
--- a/pkgs/clan-cli/clan_cli/ssh/upload.py
+++ b/pkgs/clan-cli/clan_cli/ssh/upload.py
@@ -4,7 +4,6 @@ from tempfile import TemporaryDirectory
 
 from clan_cli.cmd import Log, RunOpts
 from clan_cli.cmd import run as run_local
-from clan_cli.errors import ClanError
 from clan_cli.ssh.host import Host
 
 
@@ -17,15 +16,6 @@ def upload(
     dir_mode: int = 0o700,
     file_mode: int = 0o400,
 ) -> None:
-    # check if the remote destination is a directory (no suffix)
-    if remote_dest.suffix:
-        msg = "Only directories are allowed"
-        raise ClanError(msg)
-
-    if not local_src.is_dir():
-        msg = "Only directories are allowed"
-        raise ClanError(msg)
-
     # Create the tarball from the temporary directory
     with TemporaryDirectory(prefix="facts-upload-") as tardir:
         tar_path = Path(tardir) / "upload.tar.gz"
@@ -33,46 +23,77 @@ def upload(
         # As first uploading the tarball and then changing the permissions can lead an attacker to
         # do a race condition attack
         with tarfile.open(str(tar_path), "w:gz") as tar:
-            for root, dirs, files in local_src.walk():
-                for mdir in dirs:
-                    dir_path = Path(root) / mdir
-                    tarinfo = tar.gettarinfo(
-                        dir_path, arcname=str(dir_path.relative_to(str(local_src)))
-                    )
-                    tarinfo.mode = dir_mode
-                    tarinfo.uname = file_user
-                    tarinfo.gname = file_group
-                    tar.addfile(tarinfo)
-                for file in files:
-                    file_path = Path(root) / file
-                    tarinfo = tar.gettarinfo(
-                        file_path,
-                        arcname=str(file_path.relative_to(str(local_src))),
-                    )
-                    tarinfo.mode = file_mode
-                    tarinfo.uname = file_user
-                    tarinfo.gname = file_group
-                    with file_path.open("rb") as f:
-                        tar.addfile(tarinfo, f)
+            if local_src.is_dir():
+                # Handle directory upload
+                for root, dirs, files in local_src.walk():
+                    for mdir in dirs:
+                        dir_path = Path(root) / mdir
+                        tarinfo = tar.gettarinfo(
+                            dir_path, arcname=str(dir_path.relative_to(str(local_src)))
+                        )
+                        tarinfo.mode = dir_mode
+                        tarinfo.uname = file_user
+                        tarinfo.gname = file_group
+                        tar.addfile(tarinfo)
+                    for file in files:
+                        file_path = Path(root) / file
+                        tarinfo = tar.gettarinfo(
+                            file_path,
+                            arcname=str(file_path.relative_to(str(local_src))),
+                        )
+                        tarinfo.mode = file_mode
+                        tarinfo.uname = file_user
+                        tarinfo.gname = file_group
+                        with file_path.open("rb") as f:
+                            tar.addfile(tarinfo, f)
+            else:
+                # Handle single file upload
+                tarinfo = tar.gettarinfo(local_src, arcname=remote_dest.name)
+                tarinfo.mode = file_mode
+                tarinfo.uname = file_user
+                tarinfo.gname = file_group
+                with local_src.open("rb") as f:
+                    tar.addfile(tarinfo, f)
 
-        cmd = [
-            *host.ssh_cmd(),
-            "rm",
-            "-r",
-            str(remote_dest),
-            ";",
-            "mkdir",
-            "-m",
-            f"{dir_mode:o}",
-            "-p",
-            str(remote_dest),
-            "&&",
-            "tar",
-            "-C",
-            str(remote_dest),
-            "-xzf",
-            "-",
-        ]
+        if local_src.is_dir():
+            cmd = [
+                *host.ssh_cmd(),
+                "rm",
+                "-r",
+                str(remote_dest),
+                ";",
+                "mkdir",
+                "-m",
+                f"{dir_mode:o}",
+                "-p",
+                str(remote_dest),
+                "&&",
+                "tar",
+                "-C",
+                str(remote_dest),
+                "-xzf",
+                "-",
+            ]
+        else:
+            # For single file, extract to parent directory and ensure correct name
+            cmd = [
+                *host.ssh_cmd(),
+                "rm",
+                "-f",
+                str(remote_dest),
+                ";",
+                "mkdir",
+                "-m",
+                f"{dir_mode:o}",
+                "-p",
+                str(remote_dest.parent),
+                "&&",
+                "tar",
+                "-C",
+                str(remote_dest.parent),
+                "-xzf",
+                "-",
+            ]
 
         # TODO accept `input` to be  an IO object instead of bytes so that we don't have to read the tarfile into memory.
         with tar_path.open("rb") as f: