diff --git a/compute_endpoint/globus_compute_endpoint/cli.py b/compute_endpoint/globus_compute_endpoint/cli.py
index d52f18d19..1889adf33 100644
--- a/compute_endpoint/globus_compute_endpoint/cli.py
+++ b/compute_endpoint/globus_compute_endpoint/cli.py
@@ -490,10 +490,24 @@ def _do_start_endpoint(
             exc_type = e.__class__.__name__
             log.debug("Invalid info on stdin -- (%s) %s", exc_type, e)
 
-    if config_str is not None:
-        ep_config = load_config_yaml(config_str)
-    else:
-        ep_config = get_config(ep_dir)
+    try:
+        if config_str is not None:
+            ep_config = load_config_yaml(config_str)
+        else:
+            ep_config = get_config(ep_dir)
+    except Exception as e:
+        if isinstance(e, ClickException):
+            raise
+
+        # We've likely not exported to the log, so at least put _something_ in the
+        # logs for the human to debug; motivated by SC-28607
+        exc_type = type(e).__name__
+        msg = (
+            "Failed to find or parse endpoint configuration.  Endpoint will not"
+            f" start. ({exc_type}) {e}"
+        )
+        log.critical(msg)
+        raise
 
     if die_with_parent:
         # The endpoint cannot die with its parent if it
diff --git a/compute_endpoint/globus_compute_endpoint/endpoint/config/user_config_schema.json b/compute_endpoint/globus_compute_endpoint/endpoint/config/user_config_schema.json
index 28e84a42a..f8cfbf736 100644
--- a/compute_endpoint/globus_compute_endpoint/endpoint/config/user_config_schema.json
+++ b/compute_endpoint/globus_compute_endpoint/endpoint/config/user_config_schema.json
@@ -3,8 +3,7 @@
   "type": "object",
   "properties": {
     "endpoint_setup": { "type": "string" },
-    "endpoint_init": { "type": "string" },
     "worker_init": { "type": "string" }
   },
   "additionalProperties": true
-}
\ No newline at end of file
+}
diff --git a/compute_endpoint/globus_compute_endpoint/endpoint/config/user_config_template.yaml b/compute_endpoint/globus_compute_endpoint/endpoint/config/user_config_template.yaml
index 9cdf03d9c..a818dc994 100644
--- a/compute_endpoint/globus_compute_endpoint/endpoint/config/user_config_template.yaml
+++ b/compute_endpoint/globus_compute_endpoint/endpoint/config/user_config_template.yaml
@@ -21,6 +21,8 @@
 # There are a number of example configurations available in the documentation:
 #    https://globus-compute.readthedocs.io/en/stable/endpoints.html#example-configurations
 
+endpoint_setup: {{ endpoint_setup|default() }}
+
 engine:
   type: HighThroughputEngine
   max_workers_per_node: 1
@@ -32,8 +34,6 @@ engine:
     max_blocks: 1
     init_blocks: 1
 
-    endpoint_setup: {{ endpoint_setup|default() }}
-    endpoint_init: {{ endpoint_init|default() }}
     worker_init: {{ worker_init|default() }}
 
 # Endpoints will be restarted when a user submits new tasks to the
diff --git a/compute_endpoint/globus_compute_endpoint/endpoint/endpoint.py b/compute_endpoint/globus_compute_endpoint/endpoint/endpoint.py
index 4bb0f7a32..88c8f9cd5 100644
--- a/compute_endpoint/globus_compute_endpoint/endpoint/endpoint.py
+++ b/compute_endpoint/globus_compute_endpoint/endpoint/endpoint.py
@@ -325,12 +325,33 @@ def start_endpoint(
         reg_info: dict,
         die_with_parent: bool = False,
     ):
+        # If we are running a full detached daemon then we will send the output to
+        # log files, otherwise we can piggy back on our stdout
+        if endpoint_config.detach_endpoint:
+            stdout: t.TextIO = open(
+                os.path.join(endpoint_dir, endpoint_config.stdout), "a+"
+            )
+            stderr: t.TextIO = open(
+                os.path.join(endpoint_dir, endpoint_config.stderr), "a+"
+            )
+        else:
+            stdout = sys.stdout
+            stderr = sys.stderr
+
+        ostream = None
+        if sys.stdout.isatty():
+            ostream = sys.stdout
+        elif sys.stderr.isatty():
+            ostream = sys.stderr
+
         # This is to ensure that at least 1 executor is defined
         if not endpoint_config.executors:
-            raise Exception(
-                f"Endpoint config file at {endpoint_dir} is missing "
-                "executor definitions"
+            msg = (
+                "Endpoint configuration has no executors defined.  Endpoint will not"
+                " start."
             )
+            log.critical(msg)
+            raise ValueError(msg)
 
         pid_check = Endpoint.check_pidfile(endpoint_dir)
         # if the pidfile exists, we should return early because we don't
@@ -342,8 +363,9 @@ def start_endpoint(
                 if endpoint_config.display_name:
                     endpoint_name = endpoint_config.display_name
                 active_msg = f"Endpoint '{endpoint_name}' is already active"
-                print(active_msg)
                 log.info(active_msg)
+                if ostream:
+                    print(active_msg, file=ostream)
                 sys.exit(-1)
             else:
                 log.info(
@@ -355,21 +377,12 @@ def start_endpoint(
         if endpoint_config.endpoint_setup:
             Endpoint._run_command("endpoint_setup", endpoint_config.endpoint_setup)
 
-        result_store = ResultStore(endpoint_dir=endpoint_dir)
-
-        # Create a daemon context
-        # If we are running a full detached daemon then we will send the output to
-        # log files, otherwise we can piggy back on our stdout
-        if endpoint_config.detach_endpoint:
-            stdout: t.TextIO = open(
-                os.path.join(endpoint_dir, endpoint_config.stdout), "a+"
-            )
-            stderr: t.TextIO = open(
-                os.path.join(endpoint_dir, endpoint_config.stderr), "a+"
-            )
-        else:
-            stdout = sys.stdout
-            stderr = sys.stderr
+        try:
+            result_store = ResultStore(endpoint_dir=endpoint_dir)
+        except Exception as e:
+            exc_type = type(e).__name__
+            log.critical(f"Failed to initialize the result storage.  ({exc_type}) {e}")
+            raise
 
         try:
             pid_file = endpoint_dir / "daemon.pid"
@@ -408,7 +421,8 @@ def start_endpoint(
             except GlobusAPIError as e:
                 blocked_msg = f"Endpoint registration blocked.  [{e.text}]"
                 log.warning(blocked_msg)
-                print(blocked_msg)
+                if ostream:
+                    print(blocked_msg, file=ostream)
                 if e.http_status in (
                     HTTPStatus.CONFLICT,
                     HTTPStatus.LOCKED,
@@ -434,8 +448,9 @@ def start_endpoint(
                     "Please ensure the Globus Compute service address is reachable, "
                     "then attempt restarting the endpoint."
                 )
-                print(msg)
                 log.critical(msg)
+                if ostream:
+                    print(msg, file=ostream)
                 exit(os.EX_TEMPFAIL)
 
             ret_ep_uuid = reg_info.get("endpoint_id")
@@ -502,11 +517,6 @@ def start_endpoint(
             self.debug,
         )
 
-        ostream = None
-        if sys.stdout.isatty():
-            ostream = sys.stdout
-        elif sys.stderr.isatty():
-            ostream = sys.stderr
         if ostream:
             msg = f"Starting endpoint; registered ID: {endpoint_uuid}"
             if log_to_console:
@@ -523,7 +533,9 @@ def start_endpoint(
             # On any other system, this should make no difference (same file!)
             with open(os.devnull) as nullf:
                 if os.dup2(nullf.fileno(), 0) != 0:
-                    raise Exception("Unable to close stdin")
+                    msg = "Unable to close stdin; endpoint will not start."
+                    log.critical(msg)
+                    raise Exception(msg)
 
             setup_logging(
                 logfile=logfile,
diff --git a/compute_endpoint/tests/integration/endpoint/endpoint/test_endpoint.py b/compute_endpoint/tests/integration/endpoint/endpoint/test_endpoint.py
index 13b409932..f19bfffb6 100644
--- a/compute_endpoint/tests/integration/endpoint/endpoint/test_endpoint.py
+++ b/compute_endpoint/tests/integration/endpoint/endpoint/test_endpoint.py
@@ -44,10 +44,12 @@ def patch_compute_client(mocker):
     yield mocker.patch(f"{_MOCK_BASE}Client", return_value=gcc)
 
 
-def test_non_configured_endpoint(mocker):
-    result = CliRunner().invoke(app, ["start", "newendpoint"])
-    assert "newendpoint" in result.stdout
-    assert "not configured" in result.stdout
+def test_non_configured_endpoint(mocker, tmp_path):
+    env = {"GLOBUS_COMPUTE_USER_DIR": str(tmp_path)}
+    with mock.patch.dict(os.environ, env):
+        result = CliRunner().invoke(app, ["start", "newendpoint"])
+        assert "newendpoint" in result.stdout
+        assert "not configured" in result.stdout
 
 
 @pytest.mark.parametrize(
@@ -293,7 +295,7 @@ def test_endpoint_setup_execution(mocker, tmp_path, randomstring):
 
     endpoint_dir = None
     endpoint_uuid = None
-    endpoint_config = Config(endpoint_setup=command)
+    endpoint_config = Config(endpoint_setup=command, detach_endpoint=False)
     log_to_console = False
     no_color = True
     reg_info = {}
diff --git a/compute_endpoint/tests/integration/endpoint/endpoint/test_endpoint_manager.py b/compute_endpoint/tests/integration/endpoint/endpoint/test_endpoint_manager.py
index 88b371202..28e1eb2d9 100644
--- a/compute_endpoint/tests/integration/endpoint/endpoint/test_endpoint_manager.py
+++ b/compute_endpoint/tests/integration/endpoint/endpoint/test_endpoint_manager.py
@@ -10,7 +10,7 @@
 import pytest
 import requests
 import yaml
-from globus_compute_endpoint.endpoint.endpoint import Endpoint
+from globus_compute_endpoint.endpoint.endpoint import Config, Endpoint
 from globus_sdk import GlobusAPIError
 
 logger = logging.getLogger("mock_funcx")
@@ -333,24 +333,17 @@ def test_start_without_executors(self, mocker):
 
         mock_context.return_value.pidfile.path = ""
 
-        class mock_executors:
-            executors = None
-
-        mock_config = mock_executors()
+        config = Config(executors=[], detach_endpoint=False)
 
         manager = Endpoint()
         config_dir = pathlib.Path("/some/path/mock_endpoint")
 
         manager.configure_endpoint(config_dir, None)
-        with pytest.raises(
-            Exception,
-            match=f"Endpoint config file at {config_dir} is "
-            "missing executor definitions",
-        ):
+        with pytest.raises(ValueError, match="has no executors defined"):
             log_to_console = False
             no_color = True
             manager.start_endpoint(
-                config_dir, None, mock_config, log_to_console, no_color, reg_info={}
+                config_dir, None, config, log_to_console, no_color, reg_info={}
             )
 
     @pytest.mark.skip("This test doesn't make much sense")
diff --git a/compute_endpoint/tests/unit/test_cli_behavior.py b/compute_endpoint/tests/unit/test_cli_behavior.py
index 43192f809..aa3425290 100644
--- a/compute_endpoint/tests/unit/test_cli_behavior.py
+++ b/compute_endpoint/tests/unit/test_cli_behavior.py
@@ -363,9 +363,13 @@ def test_start_ep_incorrect_config_py(
     conf = mock_state.endpoint_config_dir / ep_name / "config.py"
 
     conf.write_text("asa asd df = 5")  # fail the import
-    with mock.patch("globus_compute_endpoint.endpoint.config.utils.log") as mock_log:
-        res = run_line(f"start {ep_name}", assert_exit_code=1)
-        assert "might be out of date" in mock_log.exception.call_args[0][0]
+    with mock.patch(f"{_MOCK_BASE}log"):
+        with mock.patch(
+            "globus_compute_endpoint.endpoint.config.utils.log"
+        ) as mock_util_log:
+            res = run_line(f"start {ep_name}", assert_exit_code=1)
+    a, _ = mock_util_log.exception.call_args
+    assert "might be out of date" in a[0]
     assert isinstance(res.exception, SyntaxError)
 
     # `coverage` demands a valid syntax file.  FBOW, then, the ordering and
diff --git a/compute_endpoint/tests/unit/test_endpoint_unit.py b/compute_endpoint/tests/unit/test_endpoint_unit.py
index b468c06eb..1a25a8826 100644
--- a/compute_endpoint/tests/unit/test_endpoint_unit.py
+++ b/compute_endpoint/tests/unit/test_endpoint_unit.py
@@ -215,6 +215,7 @@ def test_start_endpoint_network_error(
     mock_log = mocker.patch(f"{_mock_base}log")
 
     f = io.StringIO()
+    f.isatty = lambda: True
     with redirect_stdout(f):
         with pytest.raises(SystemExit) as pytest_exc:
             ep.start_endpoint(
@@ -324,7 +325,6 @@ def test_register_endpoint_blocked(
     mock_log = mocker.patch(f"{_mock_base}log")
     mock_gcc = get_standard_compute_client()
     mocker.patch(f"{_mock_base}Endpoint.get_funcx_client").return_value = mock_gcc
-    f = io.StringIO()
 
     ep, ep_dir, log_to_console, no_color, ep_conf = mock_ep_data
     ep_id = str(uuid.uuid4())
@@ -335,6 +335,8 @@ def test_register_endpoint_blocked(
         msg=some_err,
     )
 
+    f = io.StringIO()
+    f.isatty = lambda: True
     with redirect_stdout(f):
         with pytest.raises((GlobusAPIError, SystemExit)) as pytexc:
             ep.start_endpoint(
@@ -374,10 +376,10 @@ def test_register_endpoint_already_active(
     mocker.patch(f"{_mock_base}Endpoint.check_pidfile").return_value = pid_active
 
     f = io.StringIO()
+    f.isatty = lambda: True
 
     ep, ep_dir, log_to_console, no_color, ep_conf = mock_ep_data
     ep_id = str(uuid.uuid4())
-    # register_endpoint_failure_response(endpoint_id=ep_id, status_code=409)
     with redirect_stdout(f):
         with pytest.raises(SystemExit) as pytest_exc:
             ep.start_endpoint(