diff --git a/pulpcore/cli/common.py b/pulpcore/cli/common.py
index 09bbfc2ab..c067623c8 100644
--- a/pulpcore/cli/common.py
+++ b/pulpcore/cli/common.py
@@ -8,7 +8,7 @@
 
 import toml
 
-from pulpcore.cli.openapi import OpenAPI
+from pulpcore.cli.openapi import OpenAPI, OpenAPIError
 
 
 class PulpJSONEncoder(json.JSONEncoder):
@@ -38,7 +38,10 @@ def output_result(self, result: Any) -> None:
             raise NotImplementedError(f"Format '{self.format}' not implemented.")
 
     def call(self, operation_id: str, background: bool = False, *args: Any, **kwargs: Any) -> Any:
-        result = self.api.call(operation_id, *args, **kwargs)
+        try:
+            result = self.api.call(operation_id, *args, **kwargs)
+        except OpenAPIError as e:
+            raise click.ClickException(str(e))
         if "task" in result:
             task_href = result["task"]
             click.echo(f"Started task {task_href}", err=True)
@@ -55,7 +58,9 @@ def wait_for_task(self, task_href: str, timeout: int = 120) -> Any:
             if task["state"] == "completed":
                 return task
             if task["state"] == "failed":
-                raise click.ClickException("Task failed")
+                raise click.ClickException(
+                    f"Task {task_href} failed: '{task['error']['description']}'"
+                )
             if task["state"] == "canceled":
                 raise click.ClickException("Task canceled")
             click.echo(".", nl=False, err=True)
@@ -111,13 +116,16 @@ def main(
 ) -> None:
     if user and not password:
         password = click.prompt("password", hide_input=True)
-    api = OpenAPI(
-        base_url=base_url,
-        doc_path="/pulp/api/v3/docs/api.json",
-        username=user,
-        password=password,
-        validate_certs=verify_ssl,
-        refresh_cache=True,
-        debug_callback=lambda x: click.secho(x, err=True, bold=True) if verbose >= 1 else None,
-    )
+    try:
+        api = OpenAPI(
+            base_url=base_url,
+            doc_path="/pulp/api/v3/docs/api.json",
+            username=user,
+            password=password,
+            validate_certs=verify_ssl,
+            refresh_cache=True,
+            debug_callback=lambda x: click.secho(x, err=True, bold=True) if verbose >= 1 else None,
+        )
+    except OpenAPIError as e:
+        raise click.ClickException(str(e))
     ctx.obj = PulpContext(api=api, format=format)
diff --git a/pulpcore/cli/openapi.py b/pulpcore/cli/openapi.py
index 11eeec6c6..00dc2c40e 100644
--- a/pulpcore/cli/openapi.py
+++ b/pulpcore/cli/openapi.py
@@ -13,6 +13,10 @@
 import urllib3
 
 
+class OpenAPIError(Exception):
+    pass
+
+
 class OpenAPI:
     def __init__(
         self,
@@ -39,9 +43,9 @@ def __init__(
         if username and password:
             self._session.auth = (username, password)
         elif username:
-            raise Exception("Password is required if username is set.")
+            raise OpenAPIError("Password is required if username is set.")
         elif password:
-            raise Exception("Username is required if password is set.")
+            raise OpenAPIError("Username is required if password is set.")
         self._session.headers.update(headers)
         self._session.verify = validate_certs
 
@@ -76,7 +80,7 @@ def _parse_api(self, data: bytes) -> None:
         if self.api_spec.get("openapi", "").startswith("3."):
             self.openapi_version: int = 3
         else:
-            raise NotImplementedError("Unknown schema version")
+            raise OpenAPIError("Unknown schema version")
         self.operations: Dict[str, Any] = {
             method_entry["operationId"]: (method, path)
             for path, path_entry in self.api_spec["paths"].items()
@@ -85,7 +89,10 @@ def _parse_api(self, data: bytes) -> None:
         }
 
     def _download_api(self) -> bytes:
-        r: requests.Response = self._session.get(urljoin(self.base_url, self.doc_path))
+        try:
+            r: requests.Response = self._session.get(urljoin(self.base_url, self.doc_path))
+        except requests.exceptions.ConnectionError as e:
+            raise OpenAPIError(str(e))
         r.raise_for_status()
         return r.content
 
@@ -117,7 +124,7 @@ def extract_params(
             item["name"] for item in param_spec.values() if item.get("required", False)
         ]
         if any(remaining_required):
-            raise Exception(
+            raise OpenAPIError(
                 "Required parameters [{0}] missing for {1}.".format(
                     ", ".join(remaining_required), param_type
                 )
@@ -171,7 +178,7 @@ def render_body(
                     boundary=boundary
                 )
             else:
-                raise Exception("No suitable content type for file upload specified.")
+                raise OpenAPIError("No suitable content type for file upload specified.")
         elif body:
             if any((content_type.startswith("application/json") for content_type in content_types)):
                 data = str.encode(json.dumps(body))
@@ -185,7 +192,7 @@ def render_body(
                 data = str.encode(urlencode(body))
                 headers["Content-Type"] = "application/x-www-form-urlencoded"
             else:
-                raise Exception("No suitable content type for file upload specified.")
+                raise OpenAPIError("No suitable content type for request specified.")
         headers["Content-Length"] = str(len(data))
         return data
 
@@ -231,7 +238,7 @@ def call(
         )
 
         if any(parameters):
-            raise Exception(
+            raise OpenAPIError(
                 "Parameter [{names}] not available for {operation_id}.".format(
                     names=", ".join(parameters.keys()), operation_id=operation_id
                 )