diff --git a/src/commands/onboard-custom.ts b/src/commands/onboard-custom.ts
index 2da4d9d8a61..20041dd9b90 100644
--- a/src/commands/onboard-custom.ts
+++ b/src/commands/onboard-custom.ts
@@ -211,7 +211,7 @@ function resolveAliasError(params: {
   return `Alias ${normalized} already points to ${existingKey}.`;
 }
 
-function buildOpenAiHeaders(apiKey: string) {
+function buildAzureOpenAiHeaders(apiKey: string) {
   const headers: Record<string, string> = {};
   if (apiKey) {
     headers["api-key"] = apiKey;
@@ -219,6 +219,14 @@ function buildOpenAiHeaders(apiKey: string) {
   return headers;
 }
 
+function buildOpenAiHeaders(apiKey: string) {
+  const headers: Record<string, string> = {};
+  if (apiKey) {
+    headers.Authorization = `Bearer ${apiKey}`;
+  }
+  return headers;
+}
+
 function buildAnthropicHeaders(apiKey: string) {
   const headers: Record<string, string> = {
     "anthropic-version": "2023-06-01",
@@ -311,16 +319,34 @@ async function requestOpenAiVerification(params: {
     modelId: params.modelId,
     endpointPath: "chat/completions",
   });
-  return await requestVerification({
-    endpoint,
-    headers: buildOpenAiHeaders(params.apiKey),
-    body: {
-      messages: [{ role: "user", content: "Hi" }],
-      temperature: 1,
-      max_completion_tokens: DEFAULT_MAX_TOKENS,
-      stream: false,
-    },
-  });
+  const isBaseUrlAzureUrl = isAzureUrl(params.baseUrl);
+  const headers = isBaseUrlAzureUrl
+    ? buildAzureOpenAiHeaders(params.apiKey)
+    : buildOpenAiHeaders(params.apiKey);
+  if (isBaseUrlAzureUrl) {
+    return await requestVerification({
+      endpoint,
+      headers,
+      body: {
+        messages: [{ role: "user", content: "Hi" }],
+        temperature: 1,
+        max_completion_tokens: DEFAULT_MAX_TOKENS,
+        stream: false,
+      }
+    });
+  } else {
+    return await requestVerification({
+      endpoint,
+      headers,
+      body: {
+        model: params.modelId,
+        messages: [{ role: "user", content: "Hi" }],
+        temperature: 1,
+        max_tokens: 1,
+        stream: false,
+      }
+    });
+  }
 }
 
 async function requestAnthropicVerification(params: {