diff --git a/acceptance/telemetry/test.toml b/acceptance/telemetry/test.toml
index e4a577681..40a8b104d 100644
--- a/acceptance/telemetry/test.toml
+++ b/acceptance/telemetry/test.toml
@@ -1,5 +1,6 @@
 LocalOnly = true
 RecordRequests = true
+IncludeRequestHeaders = ["Authorization", "User-Agent"]
 
 [[Repls]]
 Old = '17\d{11}'
diff --git a/acceptance/telemetry/upload-command/out.requests.txt b/acceptance/telemetry/upload-command/out.requests.txt
index 9264d8bfd..3cbc17bd8 100644
--- a/acceptance/telemetry/upload-command/out.requests.txt
+++ b/acceptance/telemetry/upload-command/out.requests.txt
@@ -1,4 +1,12 @@
 {
+  "headers": {
+    "Authorization": [
+      "Bearer [DATABRICKS_TOKEN]"
+    ],
+    "User-Agent": [
+      "cli/[DEV_VERSION] databricks-sdk-go/[SDK_VERSION] go/[GO_VERSION] os/OS auth/pat"
+    ]
+  },
   "method": "POST",
   "path": "/telemetry-ext",
   "body": {
diff --git a/acceptance/telemetry/telemetry-upload-fails/out.requests.txt b/acceptance/telemetry/upload-fails/out.requests.txt
similarity index 80%
rename from acceptance/telemetry/telemetry-upload-fails/out.requests.txt
rename to acceptance/telemetry/upload-fails/out.requests.txt
index 9b23f98a4..9ac7e6245 100644
--- a/acceptance/telemetry/telemetry-upload-fails/out.requests.txt
+++ b/acceptance/telemetry/upload-fails/out.requests.txt
@@ -1,4 +1,12 @@
 {
+  "headers": {
+    "Authorization": [
+      "Bearer [DATABRICKS_TOKEN]"
+    ],
+    "User-Agent": [
+      "cli/[DEV_VERSION] databricks-sdk-go/[SDK_VERSION] go/[GO_VERSION] os/OS auth/pat"
+    ]
+  },
   "method": "POST",
   "path": "/telemetry-ext",
   "body": {
diff --git a/acceptance/telemetry/telemetry-upload-fails/out.upload_process.txt b/acceptance/telemetry/upload-fails/out.upload_process.txt
similarity index 100%
rename from acceptance/telemetry/telemetry-upload-fails/out.upload_process.txt
rename to acceptance/telemetry/upload-fails/out.upload_process.txt
diff --git a/acceptance/telemetry/telemetry-upload-fails/output.txt b/acceptance/telemetry/upload-fails/output.txt
similarity index 100%
rename from acceptance/telemetry/telemetry-upload-fails/output.txt
rename to acceptance/telemetry/upload-fails/output.txt
diff --git a/acceptance/telemetry/telemetry-upload-fails/script b/acceptance/telemetry/upload-fails/script
similarity index 100%
rename from acceptance/telemetry/telemetry-upload-fails/script
rename to acceptance/telemetry/upload-fails/script
diff --git a/acceptance/telemetry/telemetry-upload-fails/test.toml b/acceptance/telemetry/upload-fails/test.toml
similarity index 100%
rename from acceptance/telemetry/telemetry-upload-fails/test.toml
rename to acceptance/telemetry/upload-fails/test.toml
diff --git a/acceptance/telemetry/telemetry-upload-skipped/out.requests.txt b/acceptance/telemetry/upload-skipped/out.requests.txt
similarity index 100%
rename from acceptance/telemetry/telemetry-upload-skipped/out.requests.txt
rename to acceptance/telemetry/upload-skipped/out.requests.txt
diff --git a/acceptance/telemetry/telemetry-upload-skipped/output.txt b/acceptance/telemetry/upload-skipped/output.txt
similarity index 100%
rename from acceptance/telemetry/telemetry-upload-skipped/output.txt
rename to acceptance/telemetry/upload-skipped/output.txt
diff --git a/acceptance/telemetry/telemetry-upload-skipped/script b/acceptance/telemetry/upload-skipped/script
similarity index 100%
rename from acceptance/telemetry/telemetry-upload-skipped/script
rename to acceptance/telemetry/upload-skipped/script
diff --git a/acceptance/telemetry/telemetry-upload-skipped/test.toml b/acceptance/telemetry/upload-skipped/test.toml
similarity index 100%
rename from acceptance/telemetry/telemetry-upload-skipped/test.toml
rename to acceptance/telemetry/upload-skipped/test.toml
diff --git a/acceptance/telemetry/telemetry-upload-succeeds/out.requests.txt b/acceptance/telemetry/upload-succeeds/out.requests.txt
similarity index 80%
rename from acceptance/telemetry/telemetry-upload-succeeds/out.requests.txt
rename to acceptance/telemetry/upload-succeeds/out.requests.txt
index 9b23f98a4..9ac7e6245 100644
--- a/acceptance/telemetry/telemetry-upload-succeeds/out.requests.txt
+++ b/acceptance/telemetry/upload-succeeds/out.requests.txt
@@ -1,4 +1,12 @@
 {
+  "headers": {
+    "Authorization": [
+      "Bearer [DATABRICKS_TOKEN]"
+    ],
+    "User-Agent": [
+      "cli/[DEV_VERSION] databricks-sdk-go/[SDK_VERSION] go/[GO_VERSION] os/OS auth/pat"
+    ]
+  },
   "method": "POST",
   "path": "/telemetry-ext",
   "body": {
diff --git a/acceptance/telemetry/telemetry-upload-succeeds/out.upload_process.txt b/acceptance/telemetry/upload-succeeds/out.upload_process.txt
similarity index 100%
rename from acceptance/telemetry/telemetry-upload-succeeds/out.upload_process.txt
rename to acceptance/telemetry/upload-succeeds/out.upload_process.txt
diff --git a/acceptance/telemetry/telemetry-upload-succeeds/output.txt b/acceptance/telemetry/upload-succeeds/output.txt
similarity index 100%
rename from acceptance/telemetry/telemetry-upload-succeeds/output.txt
rename to acceptance/telemetry/upload-succeeds/output.txt
diff --git a/acceptance/telemetry/telemetry-upload-succeeds/script b/acceptance/telemetry/upload-succeeds/script
similarity index 82%
rename from acceptance/telemetry/telemetry-upload-succeeds/script
rename to acceptance/telemetry/upload-succeeds/script
index b11cb6e99..6aadde9f1 100644
--- a/acceptance/telemetry/telemetry-upload-succeeds/script
+++ b/acceptance/telemetry/upload-succeeds/script
@@ -1,6 +1,8 @@
 export DATABRICKS_CLI_TELEMETRY_PID_FILE=./telemetry.pid
 export DATABRICKS_CLI_TELEMETRY_UPLOAD_LOGS_FILE=./out.upload_process.txt
 
+# TODO: Move the environment variable calculation to the daemon library.
+
 trace $CLI selftest send-telemetry
 
 echo "waiting for telemetry process to finish"
diff --git a/acceptance/telemetry/telemetry-upload-succeeds/test.toml b/acceptance/telemetry/upload-succeeds/test.toml
similarity index 100%
rename from acceptance/telemetry/telemetry-upload-succeeds/test.toml
rename to acceptance/telemetry/upload-succeeds/test.toml
diff --git a/cmd/root/auth.go b/cmd/root/auth.go
index 4fcfbb4d8..5bcadfe1b 100644
--- a/cmd/root/auth.go
+++ b/cmd/root/auth.go
@@ -186,6 +186,8 @@ func workspaceClientOrPrompt(ctx context.Context, cfg *config.Config, allowPromp
 	return w, err
 }
 
+// TODO: Make upload with oauth work.
+// TODO: Move env var inheritance to the daemon library.
 func MustWorkspaceClient(cmd *cobra.Command, args []string) error {
 	cfg := &config.Config{}
 
diff --git a/libs/telemetry/upload_test.go b/libs/telemetry/upload_test.go
index 18652a5bf..cd8809519 100644
--- a/libs/telemetry/upload_test.go
+++ b/libs/telemetry/upload_test.go
@@ -14,10 +14,6 @@ import (
 	"github.com/stretchr/testify/require"
 )
 
-// TODO: Add flag to allow skipping telemetry.
-// TODO: Add verification that the telemetry process uses the correct authentication
-// credentials.
-
 func TestTelemetryUploadRetries(t *testing.T) {
 	server := testserver.New(t)
 	t.Cleanup(server.Close)