diff --git a/acceptance/acceptance_test.go b/acceptance/acceptance_test.go
index afdc42abc..0aa252900 100644
--- a/acceptance/acceptance_test.go
+++ b/acceptance/acceptance_test.go
@@ -296,6 +296,10 @@ func runTest(t *testing.T, dir, coverDir string, repls testdiff.ReplacementsCont
 				items := strings.Split(stub.Pattern, " ")
 				require.Len(t, items, 2)
 				server.Handle(items[0], items[1], func(req testserver.Request) any {
+					if stub.DelaySeconds > 0 {
+						time.Sleep(time.Duration(stub.DelaySeconds) * time.Second)
+					}
+
 					return stub.Response
 				})
 			}
diff --git a/acceptance/config_test.go b/acceptance/config_test.go
index cc5257c65..0f5bcc6a1 100644
--- a/acceptance/config_test.go
+++ b/acceptance/config_test.go
@@ -67,6 +67,9 @@ type ServerStub struct {
 
 	// The response body to return.
 	Response testserver.Response
+
+	// Artificial delay in seconds to simulate slow responses.
+	DelaySeconds int
 }
 
 // FindConfigs finds all the config relevant for this test,
diff --git a/acceptance/telemetry/partial-success-debug-logs/out.requests.txt b/acceptance/telemetry/partial-success-debug-logs/out.requests.txt
index d7b4c5713..69633b190 100644
--- a/acceptance/telemetry/partial-success-debug-logs/out.requests.txt
+++ b/acceptance/telemetry/partial-success-debug-logs/out.requests.txt
@@ -10,8 +10,8 @@
     "uploadTime": "UNIX_TIME_MILLIS",
     "items": [],
     "protoLogs": [
-      "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"execution_context\":{\"cmd_exec_id\":\"[UUID]\",\"version\":\"[DEV_VERSION]\",\"command\":\"selftest_send-telemetry\",\"operating_system\":\"[OS]\",\"execution_time_ms\":1},\"cli_test_event\":{\"name\":\"VALUE1\"}}}}",
-      "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"execution_context\":{\"cmd_exec_id\":\"[UUID]\",\"version\":\"[DEV_VERSION]\",\"command\":\"selftest_send-telemetry\",\"operating_system\":\"[OS]\",\"execution_time_ms\":1},\"cli_test_event\":{\"name\":\"VALUE2\"}}}}"
+      "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"execution_context\":{\"cmd_exec_id\":\"[UUID]\",\"version\":\"[DEV_VERSION]\",\"command\":\"selftest_send-telemetry\",\"operating_system\":\"[OS]\"},\"cli_test_event\":{\"name\":\"VALUE1\"}}}}",
+      "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"execution_context\":{\"cmd_exec_id\":\"[UUID]\",\"version\":\"[DEV_VERSION]\",\"command\":\"selftest_send-telemetry\",\"operating_system\":\"[OS]\"},\"cli_test_event\":{\"name\":\"VALUE2\"}}}}"
     ]
   }
 }
@@ -27,8 +27,8 @@
     "uploadTime": "UNIX_TIME_MILLIS",
     "items": [],
     "protoLogs": [
-      "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"execution_context\":{\"cmd_exec_id\":\"[UUID]\",\"version\":\"[DEV_VERSION]\",\"command\":\"selftest_send-telemetry\",\"operating_system\":\"[OS]\",\"execution_time_ms\":1},\"cli_test_event\":{\"name\":\"VALUE1\"}}}}",
-      "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"execution_context\":{\"cmd_exec_id\":\"[UUID]\",\"version\":\"[DEV_VERSION]\",\"command\":\"selftest_send-telemetry\",\"operating_system\":\"[OS]\",\"execution_time_ms\":1},\"cli_test_event\":{\"name\":\"VALUE2\"}}}}"
+      "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"execution_context\":{\"cmd_exec_id\":\"[UUID]\",\"version\":\"[DEV_VERSION]\",\"command\":\"selftest_send-telemetry\",\"operating_system\":\"[OS]\"},\"cli_test_event\":{\"name\":\"VALUE1\"}}}}",
+      "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"execution_context\":{\"cmd_exec_id\":\"[UUID]\",\"version\":\"[DEV_VERSION]\",\"command\":\"selftest_send-telemetry\",\"operating_system\":\"[OS]\"},\"cli_test_event\":{\"name\":\"VALUE2\"}}}}"
     ]
   }
 }
@@ -44,8 +44,8 @@
     "uploadTime": "UNIX_TIME_MILLIS",
     "items": [],
     "protoLogs": [
-      "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"execution_context\":{\"cmd_exec_id\":\"[UUID]\",\"version\":\"[DEV_VERSION]\",\"command\":\"selftest_send-telemetry\",\"operating_system\":\"[OS]\",\"execution_time_ms\":1},\"cli_test_event\":{\"name\":\"VALUE1\"}}}}",
-      "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"execution_context\":{\"cmd_exec_id\":\"[UUID]\",\"version\":\"[DEV_VERSION]\",\"command\":\"selftest_send-telemetry\",\"operating_system\":\"[OS]\",\"execution_time_ms\":1},\"cli_test_event\":{\"name\":\"VALUE2\"}}}}"
+      "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"execution_context\":{\"cmd_exec_id\":\"[UUID]\",\"version\":\"[DEV_VERSION]\",\"command\":\"selftest_send-telemetry\",\"operating_system\":\"[OS]\"},\"cli_test_event\":{\"name\":\"VALUE1\"}}}}",
+      "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"execution_context\":{\"cmd_exec_id\":\"[UUID]\",\"version\":\"[DEV_VERSION]\",\"command\":\"selftest_send-telemetry\",\"operating_system\":\"[OS]\"},\"cli_test_event\":{\"name\":\"VALUE2\"}}}}"
     ]
   }
 }
diff --git a/acceptance/telemetry/partial-success-debug-logs/output.txt b/acceptance/telemetry/partial-success-debug-logs/output.txt
index 7f74b1318..2bd9bf300 100644
--- a/acceptance/telemetry/partial-success-debug-logs/output.txt
+++ b/acceptance/telemetry/partial-success-debug-logs/output.txt
@@ -6,8 +6,8 @@ HH:MM:SS Debug: POST /telemetry-ext
 > {
 >   "items": null,
 >   "protoLogs": [
->     "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"... (232 more bytes)",
->     "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"... (232 more bytes)"
+>     "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"... (210 more bytes)",
+>     "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"... (210 more bytes)"
 >   ],
 >   "uploadTime": "UNIX_TIME_MILLIS"
 > }
@@ -22,8 +22,8 @@ HH:MM:SS Debug: POST /telemetry-ext
 > {
 >   "items": null,
 >   "protoLogs": [
->     "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"... (232 more bytes)",
->     "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"... (232 more bytes)"
+>     "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"... (210 more bytes)",
+>     "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"... (210 more bytes)"
 >   ],
 >   "uploadTime": "UNIX_TIME_MILLIS"
 > }
@@ -38,8 +38,8 @@ HH:MM:SS Debug: POST /telemetry-ext
 > {
 >   "items": null,
 >   "protoLogs": [
->     "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"... (232 more bytes)",
->     "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"... (232 more bytes)"
+>     "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"... (210 more bytes)",
+>     "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"... (210 more bytes)"
 >   ],
 >   "uploadTime": "UNIX_TIME_MILLIS"
 > }
diff --git a/acceptance/telemetry/timeout/out.requests.txt b/acceptance/telemetry/timeout/out.requests.txt
new file mode 100644
index 000000000..57574b976
--- /dev/null
+++ b/acceptance/telemetry/timeout/out.requests.txt
@@ -0,0 +1,17 @@
+{
+  "headers": {
+    "Authorization": [
+      "Bearer [DATABRICKS_TOKEN]"
+    ]
+  },
+  "method": "POST",
+  "path": "/telemetry-ext",
+  "body": {
+    "uploadTime": "UNIX_TIME_MILLIS",
+    "items": [],
+    "protoLogs": [
+      "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"execution_context\":{\"cmd_exec_id\":\"[UUID]\",\"version\":\"[DEV_VERSION]\",\"command\":\"selftest_send-telemetry\",\"operating_system\":\"[OS]\",\"execution_time_ms\":1},\"cli_test_event\":{\"name\":\"VALUE1\"}}}}",
+      "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"execution_context\":{\"cmd_exec_id\":\"[UUID]\",\"version\":\"[DEV_VERSION]\",\"command\":\"selftest_send-telemetry\",\"operating_system\":\"[OS]\",\"execution_time_ms\":1},\"cli_test_event\":{\"name\":\"VALUE2\"}}}}"
+    ]
+  }
+}
diff --git a/acceptance/telemetry/timeout/output.txt b/acceptance/telemetry/timeout/output.txt
new file mode 100644
index 000000000..8dad2627a
--- /dev/null
+++ b/acceptance/telemetry/timeout/output.txt
@@ -0,0 +1,16 @@
+
+>>> [CLI] selftest send-telemetry --debug
+HH:MM:SS Info: start pid=PID version=[DEV_VERSION] args="[CLI], selftest, send-telemetry, --debug"
+HH:MM:SS Info: completed execution pid=PID exit_code=0
+HH:MM:SS Debug: POST /telemetry-ext
+> {
+>   "items": null,
+>   "protoLogs": [
+>     "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"... (232 more bytes)",
+>     "{\"frontend_log_event_id\":\"[UUID]\",\"entry\":{\"databricks_cli_log\":{\"... (232 more bytes)"
+>   ],
+>   "uploadTime": "UNIX_TIME_MILLIS"
+> }
+< Error: Post "[DATABRICKS_URL]/telemetry-ext": context deadline exceeded pid=PID sdk=true
+HH:MM:SS Debug: non-retriable error: Post "[DATABRICKS_URL]/telemetry-ext": context deadline exceeded pid=PID sdk=true
+HH:MM:SS Debug: failed to upload telemetry: uploading telemetry logs timed out: context deadline exceeded pid=PID
diff --git a/acceptance/telemetry/timeout/script b/acceptance/telemetry/timeout/script
new file mode 100644
index 000000000..7fe85f0cd
--- /dev/null
+++ b/acceptance/telemetry/timeout/script
@@ -0,0 +1 @@
+trace $CLI selftest send-telemetry --debug
diff --git a/acceptance/telemetry/timeout/test.toml b/acceptance/telemetry/timeout/test.toml
new file mode 100644
index 000000000..65da6edb0
--- /dev/null
+++ b/acceptance/telemetry/timeout/test.toml
@@ -0,0 +1,18 @@
+[[Server]]
+Pattern = "POST /telemetry-ext"
+Response.Body = '''
+{
+    "errors": [],
+    "numProtoSuccess": 2
+}
+'''
+DelaySeconds = 5
+
+
+[[Repls]]
+Old = "(?:[01][0-9]|2[0-3]):[0-5][0-9]:[0-5][0-9]"
+New = "HH:MM:SS"
+
+[[Repls]]
+Old = "pid=[0-9]+"
+New = "pid=PID"