diff --git a/pulp-glue/pulp_glue/common/context.py b/pulp-glue/pulp_glue/common/context.py
index 7acd0860a..38adda784 100644
--- a/pulp-glue/pulp_glue/common/context.py
+++ b/pulp-glue/pulp_glue/common/context.py
@@ -1632,21 +1632,30 @@ def upload(
         self.needs_capability("upload")
         size = os.path.getsize(file.name)
         body: t.Dict[str, t.Any] = {**kwargs}
-        if not self.pulp_ctx.fake_mode:  # Skip the uploading part in fake_mode
+
+        if not self.pulp_ctx.fake_mode:
             if chunk_size > size:
+                # Small file: direct upload
                 body["file"] = file
-            elif self.pulp_ctx.has_plugin(PluginRequirement("core", specifier=">=3.20.0")):
-                from pulp_glue.core.context import PulpUploadContext
-
-                upload_href = PulpUploadContext(self.pulp_ctx).upload_file(file, chunk_size)
-                body["upload"] = upload_href
             else:
-                from pulp_glue.core.context import PulpArtifactContext
+                # Large file: chunked upload
+                if self.pulp_ctx.has_plugin(PluginRequirement("core", specifier=">=3.20.0")):
+                    from pulp_glue.core.context import PulpUploadContext
+
+                    upload_href = PulpUploadContext(self.pulp_ctx).upload_file(file, chunk_size)
+                    body["upload"] = upload_href
+                else:
+                    from pulp_glue.core.context import PulpArtifactContext
+
+                    artifact_href = PulpArtifactContext(self.pulp_ctx).upload(file, chunk_size)
+                    body["artifact"] = artifact_href
+
+        # If no repository is provided, use synchronous upload endpoint
+        if repository is None:
+            return self.call("upload", body=body)
 
-                artifact_href = PulpArtifactContext(self.pulp_ctx).upload(file, chunk_size)
-                body["artifact"] = artifact_href
-            if repository:
-                body["repository"] = repository
+        # Repository is specified: use create endpoint (async path)
+        body["repository"] = repository
         return self.create(body=body)
 
 
diff --git a/pulpcore/cli/rpm/content.py b/pulpcore/cli/rpm/content.py
index 9dbc607a9..04c3726f0 100644
--- a/pulpcore/cli/rpm/content.py
+++ b/pulpcore/cli/rpm/content.py
@@ -389,11 +389,14 @@ def upload(
                 _("You must specify one (and only one) of --file or --directory.")
             )
 
-        # Sanity: If directory, repository required
+        # Sanity: If directory with temp repo, repository required
         final_dest_repo_ctx = kwargs["repository"]
-        if directory and not final_dest_repo_ctx:
+        if directory and kwargs["use_temp_repository"] and not final_dest_repo_ctx:
             raise click.ClickException(
-                _("You must specify a --repository to use --directory uploads.")
+                _(
+                    "You must specify a --repository to use --use-temp-repository "
+                    "with --directory uploads."
+                )
             )
 
         # Sanity: ignore publish|use_temp unless directory has been specified
@@ -416,17 +419,20 @@ def upload(
             )
         else:
             # Upload a directory-full of RPMs
+            dest_repo_ctx = None
             try:
                 dest_repo_ctx = _determine_upload_repository(final_dest_repo_ctx, pulp_ctx, use_tmp)
                 result = _upload_rpms(entity_ctx, dest_repo_ctx, directory, chunk_size)
-                if use_tmp:
+                if use_tmp and dest_repo_ctx:
                     result = _copy_to_final(dest_repo_ctx, final_dest_repo_ctx, pulp_ctx)
             finally:
                 if use_tmp and dest_repo_ctx:
                     # Remove the tmp-upload repo
                     dest_repo_ctx.delete()
 
-        final_version_number = _latest_version_number(final_dest_repo_ctx)
+        final_version_number = (
+            _latest_version_number(final_dest_repo_ctx) if final_dest_repo_ctx else None
+        )
         if final_version_number:
             click.echo(
                 _(
@@ -488,7 +494,7 @@ def _copy_to_final(
 
 def _upload_rpms(
     entity_ctx: PulpContentContext,
-    dest_repo_ctx: PulpRpmRepositoryContext,
+    dest_repo_ctx: t.Optional[PulpRpmRepositoryContext],
     directory: t.Any,
     chunk_size: int,
 ) -> t.Any:
@@ -496,15 +502,28 @@ def _upload_rpms(
     rpm_names = glob.glob(rpms_path)
     if not rpm_names:
         raise click.ClickException(_("Directory {} has no .rpm files in it.").format(directory))
-    click.echo(
-        _(
-            "About to upload {} files for {}.".format(
-                len(rpm_names),
-                dest_repo_ctx.entity["name"],
-            )
-        ),
-        err=True,
-    )
+
+    # Build message based on whether we have a repository or not
+    if dest_repo_ctx:
+        click.echo(
+            _(
+                "About to upload {} files for {}.".format(
+                    len(rpm_names),
+                    dest_repo_ctx.entity["name"],
+                )
+            ),
+            err=True,
+        )
+    else:
+        click.echo(
+            _(
+                "About to upload {} files from {}.".format(
+                    len(rpm_names),
+                    directory,
+                )
+            ),
+            err=True,
+        )
     # Upload all *.rpm into the destination
     successful_uploads = 0
     for name in rpm_names:
@@ -525,9 +544,11 @@ def _upload_rpms(
 
 
 def _determine_upload_repository(
-    final_dest_repo_ctx: PulpRpmRepositoryContext, pulp_ctx: PulpCLIContext, use_tmp: bool
-) -> PulpRpmRepositoryContext:
-    if use_tmp:
+    final_dest_repo_ctx: t.Optional[PulpRpmRepositoryContext],
+    pulp_ctx: PulpCLIContext,
+    use_tmp: bool,
+) -> t.Optional[PulpRpmRepositoryContext]:
+    if use_tmp and final_dest_repo_ctx:
         dest_repo_ctx = PulpRpmRepositoryContext(pulp_ctx)
         body: t.Dict[str, t.Any] = {
             "name": f"uploadtmp_{final_dest_repo_ctx.entity['name']}_{uuid4()}",