diff --git a/pkgs/clan-cli/clan_cli/ssh/upload.py b/pkgs/clan-cli/clan_cli/ssh/upload.py
index 8b04b8fc8..3cdba60b4 100644
--- a/pkgs/clan-cli/clan_cli/ssh/upload.py
+++ b/pkgs/clan-cli/clan_cli/ssh/upload.py
@@ -66,7 +66,14 @@ def upload(
         if host.user != "root":
             sudo = "sudo -- "
 
-        cmd = 'rm -rf "$0" && mkdir -m "$1" -p "$0" && tar -C "$0" -xzf -'
+        cmd = None
+        if local_src.is_dir():
+            cmd = 'rm -rf "$0" && mkdir -m "$1" -p "$0" && tar -C "$0" -xzf -'
+        elif local_src.is_file():
+            cmd = 'rm -f "$0" && tar -C "$(dirname "$0")" -xzf -'
+        else:
+            msg = f"Unsupported source type: {local_src}"
+            raise ClanError(msg)
 
         # 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:
diff --git a/pkgs/clan-cli/clan_cli/tests/test_secrets_upload.py b/pkgs/clan-cli/clan_cli/tests/test_secrets_upload.py
index 4a25c30d0..677a34e08 100644
--- a/pkgs/clan-cli/clan_cli/tests/test_secrets_upload.py
+++ b/pkgs/clan-cli/clan_cli/tests/test_secrets_upload.py
@@ -1,7 +1,9 @@
+from pathlib import Path
 from typing import TYPE_CHECKING
 
 import pytest
-from clan_cli.ssh.host import Host
+from clan_cli.ssh.host import Host, HostKeyCheck
+from clan_cli.ssh.upload import upload
 from clan_cli.tests.fixtures_flakes import ClanFlake
 from clan_cli.tests.helpers import cli
 
@@ -9,6 +11,25 @@ if TYPE_CHECKING:
     from .age_keys import KeyPair
 
 
+@pytest.mark.with_core
+def test_upload_single_file(
+    monkeypatch: pytest.MonkeyPatch,
+    temporary_home: Path,
+    hosts: list[Host],
+) -> None:
+    host = hosts[0]
+    host.host_key_check = HostKeyCheck.NONE
+
+    src_file = temporary_home / "test.txt"
+    src_file.write_text("test")
+    dest_file = temporary_home / "test_dest.txt"
+
+    upload(host, src_file, dest_file)
+
+    assert dest_file.exists()
+    assert dest_file.read_text() == "test"
+
+
 @pytest.mark.with_core
 def test_secrets_upload(
     monkeypatch: pytest.MonkeyPatch,