diff --git a/crates/goose-cli/src/commands/configure.rs b/crates/goose-cli/src/commands/configure.rs
index cf26f3acb6ab..8e652e3f4abb 100644
--- a/crates/goose-cli/src/commands/configure.rs
+++ b/crates/goose-cli/src/commands/configure.rs
@@ -1718,7 +1718,7 @@ fn add_provider() -> anyhow::Result<()> {
         .interact()?;
 
     let api_url: String = cliclack::input("Provider API URL:")
-        .placeholder("https://api.example.com/v1/messages")
+        .placeholder("https://api.example.com/v1")
         .validate(|input: &String| {
             if !input.starts_with("http://") && !input.starts_with("https://") {
                 Err("URL must start with either http:// or https://")
diff --git a/crates/goose/src/providers/openai.rs b/crates/goose/src/providers/openai.rs
index f6fe3042bc03..61e6afee25fe 100644
--- a/crates/goose/src/providers/openai.rs
+++ b/crates/goose/src/providers/openai.rs
@@ -154,7 +154,7 @@ impl OpenAiProvider {
             format!("{}://{}", url.scheme(), url.host_str().unwrap_or(""))
         };
         let base_path = url.path().trim_start_matches('/').to_string();
-        let base_path = if base_path.is_empty() {
+        let base_path = if base_path.is_empty() || base_path == "v1" || base_path == "v1/" {
             "v1/chat/completions".to_string()
         } else {
             base_path
diff --git a/ui/desktop/src/components/settings/providers/modal/subcomponents/forms/CustomProviderForm.tsx b/ui/desktop/src/components/settings/providers/modal/subcomponents/forms/CustomProviderForm.tsx
index 28c8b4a13191..e45a503522fa 100644
--- a/ui/desktop/src/components/settings/providers/modal/subcomponents/forms/CustomProviderForm.tsx
+++ b/ui/desktop/src/components/settings/providers/modal/subcomponents/forms/CustomProviderForm.tsx
@@ -158,7 +158,7 @@ export default function CustomProviderForm({
               id="api-url"
               value={apiUrl}
               onChange={(e) => setApiUrl(e.target.value)}
-              placeholder="https://api.example.com/v1/messages"
+              placeholder="https://api.example.com/v1"
               aria-invalid={!!validationErrors.apiUrl}
               aria-describedby={validationErrors.apiUrl ? 'api-url-error' : undefined}
               className={validationErrors.apiUrl ? 'border-red-500' : ''}