diff --git a/Cargo.lock b/Cargo.lock
index 52b017b876..c707c3349d 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -6951,6 +6951,7 @@ dependencies = [
  "serde_json",
  "smol",
  "strum",
+ "thiserror 1.0.69",
  "ui",
  "util",
 ]
diff --git a/crates/assistant/src/assistant_panel.rs b/crates/assistant/src/assistant_panel.rs
index 585f809e25..ecf2e2c421 100644
--- a/crates/assistant/src/assistant_panel.rs
+++ b/crates/assistant/src/assistant_panel.rs
@@ -20,7 +20,9 @@ use gpui::{
     Subscription, Task, UpdateGlobal, WeakEntity,
 };
 use language::LanguageRegistry;
-use language_model::{LanguageModelProviderId, LanguageModelRegistry, ZED_CLOUD_PROVIDER_ID};
+use language_model::{
+    AuthenticateError, LanguageModelProviderId, LanguageModelRegistry, ZED_CLOUD_PROVIDER_ID,
+};
 use project::Project;
 use prompt_library::{open_prompt_library, PromptBuilder, PromptLibrary};
 use search::{buffer_search::DivRegistrar, BufferSearchBar};
@@ -1156,7 +1158,10 @@ impl AssistantPanel {
             .map_or(false, |provider| provider.is_authenticated(cx))
     }
 
-    fn authenticate(&mut self, cx: &mut Context<Self>) -> Option<Task<Result<()>>> {
+    fn authenticate(
+        &mut self,
+        cx: &mut Context<Self>,
+    ) -> Option<Task<Result<(), AuthenticateError>>> {
         LanguageModelRegistry::read_global(cx)
             .active_provider()
             .map_or(None, |provider| Some(provider.authenticate(cx)))
diff --git a/crates/language_model/Cargo.toml b/crates/language_model/Cargo.toml
index 7b570a54f7..51f205dced 100644
--- a/crates/language_model/Cargo.toml
+++ b/crates/language_model/Cargo.toml
@@ -38,6 +38,7 @@ serde.workspace = true
 serde_json.workspace = true
 smol.workspace = true
 strum.workspace = true
+thiserror.workspace = true
 ui.workspace = true
 util.workspace = true
 
diff --git a/crates/language_model/src/fake_provider.rs b/crates/language_model/src/fake_provider.rs
index c3eca1a2f4..a955638b21 100644
--- a/crates/language_model/src/fake_provider.rs
+++ b/crates/language_model/src/fake_provider.rs
@@ -1,6 +1,6 @@
 use crate::{
-    LanguageModel, LanguageModelCompletionEvent, LanguageModelId, LanguageModelName,
-    LanguageModelProvider, LanguageModelProviderId, LanguageModelProviderName,
+    AuthenticateError, LanguageModel, LanguageModelCompletionEvent, LanguageModelId,
+    LanguageModelName, LanguageModelProvider, LanguageModelProviderId, LanguageModelProviderName,
     LanguageModelProviderState, LanguageModelRequest,
 };
 use futures::{channel::mpsc, future::BoxFuture, stream::BoxStream, FutureExt, StreamExt};
@@ -54,7 +54,7 @@ impl LanguageModelProvider for FakeLanguageModelProvider {
         true
     }
 
-    fn authenticate(&self, _: &mut App) -> Task<Result<()>> {
+    fn authenticate(&self, _: &mut App) -> Task<Result<(), AuthenticateError>> {
         Task::ready(Ok(()))
     }
 
diff --git a/crates/language_model/src/language_model.rs b/crates/language_model/src/language_model.rs
index 4cdf432572..6219fda739 100644
--- a/crates/language_model/src/language_model.rs
+++ b/crates/language_model/src/language_model.rs
@@ -21,6 +21,7 @@ use schemars::JsonSchema;
 use serde::{de::DeserializeOwned, Deserialize, Serialize};
 use std::fmt;
 use std::{future::Future, sync::Arc};
+use thiserror::Error;
 use ui::IconName;
 
 pub const ZED_CLOUD_PROVIDER_ID: &str = "zed.dev";
@@ -231,6 +232,15 @@ pub trait LanguageModelTool: 'static + DeserializeOwned + JsonSchema {
     fn description() -> String;
 }
 
+/// An error that occurred when trying to authenticate the language model provider.
+#[derive(Debug, Error)]
+pub enum AuthenticateError {
+    #[error("credentials not found")]
+    CredentialsNotFound,
+    #[error(transparent)]
+    Other(#[from] anyhow::Error),
+}
+
 pub trait LanguageModelProvider: 'static {
     fn id(&self) -> LanguageModelProviderId;
     fn name(&self) -> LanguageModelProviderName;
@@ -240,7 +250,7 @@ pub trait LanguageModelProvider: 'static {
     fn provided_models(&self, cx: &App) -> Vec<Arc<dyn LanguageModel>>;
     fn load_model(&self, _model: Arc<dyn LanguageModel>, _cx: &App) {}
     fn is_authenticated(&self, cx: &App) -> bool;
-    fn authenticate(&self, cx: &mut App) -> Task<Result<()>>;
+    fn authenticate(&self, cx: &mut App) -> Task<Result<(), AuthenticateError>>;
     fn configuration_view(&self, window: &mut Window, cx: &mut App) -> AnyView;
     fn must_accept_terms(&self, _cx: &App) -> bool {
         false
diff --git a/crates/language_models/src/provider/anthropic.rs b/crates/language_models/src/provider/anthropic.rs
index 835229ab63..e990868b9c 100644
--- a/crates/language_models/src/provider/anthropic.rs
+++ b/crates/language_models/src/provider/anthropic.rs
@@ -10,8 +10,8 @@ use gpui::{
 };
 use http_client::HttpClient;
 use language_model::{
-    LanguageModel, LanguageModelCacheConfiguration, LanguageModelId, LanguageModelName,
-    LanguageModelProvider, LanguageModelProviderId, LanguageModelProviderName,
+    AuthenticateError, LanguageModel, LanguageModelCacheConfiguration, LanguageModelId,
+    LanguageModelName, LanguageModelProvider, LanguageModelProviderId, LanguageModelProviderName,
     LanguageModelProviderState, LanguageModelRequest, RateLimiter, Role,
 };
 use language_model::{LanguageModelCompletionEvent, LanguageModelToolUse, StopReason};
@@ -105,34 +105,38 @@ impl State {
         self.api_key.is_some()
     }
 
-    fn authenticate(&self, cx: &mut Context<Self>) -> Task<Result<()>> {
+    fn authenticate(&self, cx: &mut Context<Self>) -> Task<Result<(), AuthenticateError>> {
         if self.is_authenticated() {
-            Task::ready(Ok(()))
-        } else {
-            let api_url = AllLanguageModelSettings::get_global(cx)
-                .anthropic
-                .api_url
-                .clone();
-
-            cx.spawn(|this, mut cx| async move {
-                let (api_key, from_env) = if let Ok(api_key) = std::env::var(ANTHROPIC_API_KEY_VAR)
-                {
-                    (api_key, true)
-                } else {
-                    let (_, api_key) = cx
-                        .update(|cx| cx.read_credentials(&api_url))?
-                        .await?
-                        .ok_or_else(|| anyhow!("credentials not found"))?;
-                    (String::from_utf8(api_key)?, false)
-                };
-
-                this.update(&mut cx, |this, cx| {
-                    this.api_key = Some(api_key);
-                    this.api_key_from_env = from_env;
-                    cx.notify();
-                })
-            })
+            return Task::ready(Ok(()));
         }
+
+        let api_url = AllLanguageModelSettings::get_global(cx)
+            .anthropic
+            .api_url
+            .clone();
+
+        cx.spawn(|this, mut cx| async move {
+            let (api_key, from_env) = if let Ok(api_key) = std::env::var(ANTHROPIC_API_KEY_VAR) {
+                (api_key, true)
+            } else {
+                let (_, api_key) = cx
+                    .update(|cx| cx.read_credentials(&api_url))?
+                    .await?
+                    .ok_or(AuthenticateError::CredentialsNotFound)?;
+                (
+                    String::from_utf8(api_key).context("invalid {PROVIDER_NAME} API key")?,
+                    false,
+                )
+            };
+
+            this.update(&mut cx, |this, cx| {
+                this.api_key = Some(api_key);
+                this.api_key_from_env = from_env;
+                cx.notify();
+            })?;
+
+            Ok(())
+        })
     }
 }
 
@@ -226,7 +230,7 @@ impl LanguageModelProvider for AnthropicLanguageModelProvider {
         self.state.read(cx).is_authenticated()
     }
 
-    fn authenticate(&self, cx: &mut App) -> Task<Result<()>> {
+    fn authenticate(&self, cx: &mut App) -> Task<Result<(), AuthenticateError>> {
         self.state.update(cx, |state, cx| state.authenticate(cx))
     }
 
diff --git a/crates/language_models/src/provider/cloud.rs b/crates/language_models/src/provider/cloud.rs
index 27d0e12596..05544f40db 100644
--- a/crates/language_models/src/provider/cloud.rs
+++ b/crates/language_models/src/provider/cloud.rs
@@ -17,9 +17,10 @@ use gpui::{
 };
 use http_client::{AsyncBody, HttpClient, Method, Response, StatusCode};
 use language_model::{
-    CloudModel, LanguageModel, LanguageModelCacheConfiguration, LanguageModelId, LanguageModelName,
-    LanguageModelProviderId, LanguageModelProviderName, LanguageModelProviderState,
-    LanguageModelProviderTosView, LanguageModelRequest, RateLimiter, ZED_CLOUD_PROVIDER_ID,
+    AuthenticateError, CloudModel, LanguageModel, LanguageModelCacheConfiguration, LanguageModelId,
+    LanguageModelName, LanguageModelProviderId, LanguageModelProviderName,
+    LanguageModelProviderState, LanguageModelProviderTosView, LanguageModelRequest, RateLimiter,
+    ZED_CLOUD_PROVIDER_ID,
 };
 use language_model::{
     LanguageModelAvailability, LanguageModelCompletionEvent, LanguageModelProvider,
@@ -363,7 +364,7 @@ impl LanguageModelProvider for CloudLanguageModelProvider {
         !self.state.read(cx).is_signed_out()
     }
 
-    fn authenticate(&self, _cx: &mut App) -> Task<Result<()>> {
+    fn authenticate(&self, _cx: &mut App) -> Task<Result<(), AuthenticateError>> {
         Task::ready(Ok(()))
     }
 
diff --git a/crates/language_models/src/provider/copilot_chat.rs b/crates/language_models/src/provider/copilot_chat.rs
index 6efac131e9..1c4a4273ac 100644
--- a/crates/language_models/src/provider/copilot_chat.rs
+++ b/crates/language_models/src/provider/copilot_chat.rs
@@ -15,8 +15,8 @@ use gpui::{
     Task, Transformation,
 };
 use language_model::{
-    LanguageModel, LanguageModelCompletionEvent, LanguageModelId, LanguageModelName,
-    LanguageModelProvider, LanguageModelProviderId, LanguageModelProviderName,
+    AuthenticateError, LanguageModel, LanguageModelCompletionEvent, LanguageModelId,
+    LanguageModelName, LanguageModelProvider, LanguageModelProviderId, LanguageModelProviderName,
     LanguageModelProviderState, LanguageModelRequest, RateLimiter, Role,
 };
 use settings::SettingsStore;
@@ -104,26 +104,28 @@ impl LanguageModelProvider for CopilotChatLanguageModelProvider {
         self.state.read(cx).is_authenticated(cx)
     }
 
-    fn authenticate(&self, cx: &mut App) -> Task<Result<()>> {
-        let result = if self.is_authenticated(cx) {
-            Ok(())
-        } else if let Some(copilot) = Copilot::global(cx) {
-            let error_msg = match copilot.read(cx).status() {
-                Status::Disabled => anyhow::anyhow!("Copilot must be enabled for Copilot Chat to work. Please enable Copilot and try again."),
-                Status::Error(e) => anyhow::anyhow!(format!("Received the following error while signing into Copilot: {e}")),
-                Status::Starting { task: _ } => anyhow::anyhow!("Copilot is still starting, please wait for Copilot to start then try again"),
-                Status::Unauthorized => anyhow::anyhow!("Unable to authorize with Copilot. Please make sure that you have an active Copilot and Copilot Chat subscription."),
-                Status::Authorized => return Task::ready(Ok(())),
-                Status::SignedOut => anyhow::anyhow!("You have signed out of Copilot. Please sign in to Copilot and try again."),
-                Status::SigningIn { prompt: _ } => anyhow::anyhow!("Still signing into Copilot..."),
-            };
-            Err(error_msg)
-        } else {
-            Err(anyhow::anyhow!(
-                "Copilot must be enabled for Copilot Chat to work. Please enable Copilot and try again."
-            ))
+    fn authenticate(&self, cx: &mut App) -> Task<Result<(), AuthenticateError>> {
+        if self.is_authenticated(cx) {
+            return Task::ready(Ok(()));
         };
-        Task::ready(result)
+
+        let Some(copilot) = Copilot::global(cx) else {
+            return Task::ready( Err(anyhow!(
+                "Copilot must be enabled for Copilot Chat to work. Please enable Copilot and try again."
+            ).into()));
+        };
+
+        let err = match copilot.read(cx).status() {
+            Status::Authorized => return Task::ready(Ok(())),
+            Status::Disabled => anyhow!("Copilot must be enabled for Copilot Chat to work. Please enable Copilot and try again."),
+            Status::Error(err) => anyhow!(format!("Received the following error while signing into Copilot: {err}")),
+            Status::Starting { task: _ } => anyhow!("Copilot is still starting, please wait for Copilot to start then try again"),
+            Status::Unauthorized => anyhow!("Unable to authorize with Copilot. Please make sure that you have an active Copilot and Copilot Chat subscription."),
+            Status::SignedOut => anyhow!("You have signed out of Copilot. Please sign in to Copilot and try again."),
+            Status::SigningIn { prompt: _ } => anyhow!("Still signing into Copilot..."),
+        };
+
+        Task::ready(Err(err.into()))
     }
 
     fn configuration_view(&self, _: &mut Window, cx: &mut App) -> AnyView {
diff --git a/crates/language_models/src/provider/deepseek.rs b/crates/language_models/src/provider/deepseek.rs
index ef7a60deeb..9a65273d12 100644
--- a/crates/language_models/src/provider/deepseek.rs
+++ b/crates/language_models/src/provider/deepseek.rs
@@ -1,4 +1,4 @@
-use anyhow::{anyhow, Result};
+use anyhow::{anyhow, Context as _, Result};
 use collections::BTreeMap;
 use editor::{Editor, EditorElement, EditorStyle};
 use futures::{future::BoxFuture, stream::BoxStream, FutureExt, StreamExt};
@@ -8,8 +8,8 @@ use gpui::{
 };
 use http_client::HttpClient;
 use language_model::{
-    LanguageModel, LanguageModelCompletionEvent, LanguageModelId, LanguageModelName,
-    LanguageModelProvider, LanguageModelProviderId, LanguageModelProviderName,
+    AuthenticateError, LanguageModel, LanguageModelCompletionEvent, LanguageModelId,
+    LanguageModelName, LanguageModelProvider, LanguageModelProviderId, LanguageModelProviderName,
     LanguageModelProviderState, LanguageModelRequest, RateLimiter, Role,
 };
 use schemars::JsonSchema;
@@ -83,33 +83,38 @@ impl State {
         })
     }
 
-    fn authenticate(&self, cx: &mut Context<Self>) -> Task<Result<()>> {
+    fn authenticate(&self, cx: &mut Context<Self>) -> Task<Result<(), AuthenticateError>> {
         if self.is_authenticated() {
-            Task::ready(Ok(()))
-        } else {
-            let api_url = AllLanguageModelSettings::get_global(cx)
-                .deepseek
-                .api_url
-                .clone();
-
-            cx.spawn(|this, mut cx| async move {
-                let (api_key, from_env) = if let Ok(api_key) = std::env::var(DEEPSEEK_API_KEY_VAR) {
-                    (api_key, true)
-                } else {
-                    let (_, api_key) = cx
-                        .update(|cx| cx.read_credentials(&api_url))?
-                        .await?
-                        .ok_or_else(|| anyhow!("credentials not found"))?;
-                    (String::from_utf8(api_key)?, false)
-                };
-
-                this.update(&mut cx, |this, cx| {
-                    this.api_key = Some(api_key);
-                    this.api_key_from_env = from_env;
-                    cx.notify();
-                })
-            })
+            return Task::ready(Ok(()));
         }
+
+        let api_url = AllLanguageModelSettings::get_global(cx)
+            .deepseek
+            .api_url
+            .clone();
+
+        cx.spawn(|this, mut cx| async move {
+            let (api_key, from_env) = if let Ok(api_key) = std::env::var(DEEPSEEK_API_KEY_VAR) {
+                (api_key, true)
+            } else {
+                let (_, api_key) = cx
+                    .update(|cx| cx.read_credentials(&api_url))?
+                    .await?
+                    .ok_or(AuthenticateError::CredentialsNotFound)?;
+                (
+                    String::from_utf8(api_key).context("invalid {PROVIDER_NAME} API key")?,
+                    false,
+                )
+            };
+
+            this.update(&mut cx, |this, cx| {
+                this.api_key = Some(api_key);
+                this.api_key_from_env = from_env;
+                cx.notify();
+            })?;
+
+            Ok(())
+        })
     }
 }
 
@@ -188,7 +193,7 @@ impl LanguageModelProvider for DeepSeekLanguageModelProvider {
         self.state.read(cx).is_authenticated()
     }
 
-    fn authenticate(&self, cx: &mut App) -> Task<Result<()>> {
+    fn authenticate(&self, cx: &mut App) -> Task<Result<(), AuthenticateError>> {
         self.state.update(cx, |state, cx| state.authenticate(cx))
     }
 
@@ -322,6 +327,7 @@ impl LanguageModel for DeepSeekLanguageModel {
         }
         .boxed()
     }
+
     fn use_any_tool(
         &self,
         request: LanguageModelRequest,
diff --git a/crates/language_models/src/provider/google.rs b/crates/language_models/src/provider/google.rs
index 48960e8ecd..d7a6e8ba2a 100644
--- a/crates/language_models/src/provider/google.rs
+++ b/crates/language_models/src/provider/google.rs
@@ -1,4 +1,4 @@
-use anyhow::{anyhow, Result};
+use anyhow::{anyhow, Context as _, Result};
 use collections::BTreeMap;
 use editor::{Editor, EditorElement, EditorStyle};
 use futures::{future::BoxFuture, FutureExt, StreamExt};
@@ -7,7 +7,7 @@ use gpui::{
     AnyView, App, AsyncApp, Context, Entity, FontStyle, Subscription, Task, TextStyle, WhiteSpace,
 };
 use http_client::HttpClient;
-use language_model::LanguageModelCompletionEvent;
+use language_model::{AuthenticateError, LanguageModelCompletionEvent};
 use language_model::{
     LanguageModel, LanguageModelId, LanguageModelName, LanguageModelProvider,
     LanguageModelProviderId, LanguageModelProviderName, LanguageModelProviderState,
@@ -85,34 +85,38 @@ impl State {
         })
     }
 
-    fn authenticate(&self, cx: &mut Context<Self>) -> Task<Result<()>> {
+    fn authenticate(&self, cx: &mut Context<Self>) -> Task<Result<(), AuthenticateError>> {
         if self.is_authenticated() {
-            Task::ready(Ok(()))
-        } else {
-            let api_url = AllLanguageModelSettings::get_global(cx)
-                .google
-                .api_url
-                .clone();
-
-            cx.spawn(|this, mut cx| async move {
-                let (api_key, from_env) = if let Ok(api_key) = std::env::var(GOOGLE_AI_API_KEY_VAR)
-                {
-                    (api_key, true)
-                } else {
-                    let (_, api_key) = cx
-                        .update(|cx| cx.read_credentials(&api_url))?
-                        .await?
-                        .ok_or_else(|| anyhow!("credentials not found"))?;
-                    (String::from_utf8(api_key)?, false)
-                };
-
-                this.update(&mut cx, |this, cx| {
-                    this.api_key = Some(api_key);
-                    this.api_key_from_env = from_env;
-                    cx.notify();
-                })
-            })
+            return Task::ready(Ok(()));
         }
+
+        let api_url = AllLanguageModelSettings::get_global(cx)
+            .google
+            .api_url
+            .clone();
+
+        cx.spawn(|this, mut cx| async move {
+            let (api_key, from_env) = if let Ok(api_key) = std::env::var(GOOGLE_AI_API_KEY_VAR) {
+                (api_key, true)
+            } else {
+                let (_, api_key) = cx
+                    .update(|cx| cx.read_credentials(&api_url))?
+                    .await?
+                    .ok_or(AuthenticateError::CredentialsNotFound)?;
+                (
+                    String::from_utf8(api_key).context("invalid {PROVIDER_NAME} API key")?,
+                    false,
+                )
+            };
+
+            this.update(&mut cx, |this, cx| {
+                this.api_key = Some(api_key);
+                this.api_key_from_env = from_env;
+                cx.notify();
+            })?;
+
+            Ok(())
+        })
     }
 }
 
@@ -194,7 +198,7 @@ impl LanguageModelProvider for GoogleLanguageModelProvider {
         self.state.read(cx).is_authenticated()
     }
 
-    fn authenticate(&self, cx: &mut App) -> Task<Result<()>> {
+    fn authenticate(&self, cx: &mut App) -> Task<Result<(), AuthenticateError>> {
         self.state.update(cx, |state, cx| state.authenticate(cx))
     }
 
diff --git a/crates/language_models/src/provider/lmstudio.rs b/crates/language_models/src/provider/lmstudio.rs
index 9096c3fb32..76832a44e1 100644
--- a/crates/language_models/src/provider/lmstudio.rs
+++ b/crates/language_models/src/provider/lmstudio.rs
@@ -2,7 +2,7 @@ use anyhow::{anyhow, Result};
 use futures::{future::BoxFuture, stream::BoxStream, FutureExt, StreamExt};
 use gpui::{AnyView, App, AsyncApp, Context, Subscription, Task};
 use http_client::HttpClient;
-use language_model::LanguageModelCompletionEvent;
+use language_model::{AuthenticateError, LanguageModelCompletionEvent};
 use language_model::{
     LanguageModel, LanguageModelId, LanguageModelName, LanguageModelProvider,
     LanguageModelProviderId, LanguageModelProviderName, LanguageModelProviderState,
@@ -90,12 +90,13 @@ impl State {
         self.fetch_model_task.replace(task);
     }
 
-    fn authenticate(&mut self, cx: &mut Context<Self>) -> Task<Result<()>> {
+    fn authenticate(&mut self, cx: &mut Context<Self>) -> Task<Result<(), AuthenticateError>> {
         if self.is_authenticated() {
-            Task::ready(Ok(()))
-        } else {
-            self.fetch_models(cx)
+            return Task::ready(Ok(()));
         }
+
+        let fetch_models_task = self.fetch_models(cx);
+        cx.spawn(|_this, _cx| async move { Ok(fetch_models_task.await?) })
     }
 }
 
@@ -201,7 +202,7 @@ impl LanguageModelProvider for LmStudioLanguageModelProvider {
         self.state.read(cx).is_authenticated()
     }
 
-    fn authenticate(&self, cx: &mut App) -> Task<Result<()>> {
+    fn authenticate(&self, cx: &mut App) -> Task<Result<(), AuthenticateError>> {
         self.state.update(cx, |state, cx| state.authenticate(cx))
     }
 
diff --git a/crates/language_models/src/provider/mistral.rs b/crates/language_models/src/provider/mistral.rs
index 383bff1437..a5cc3dac16 100644
--- a/crates/language_models/src/provider/mistral.rs
+++ b/crates/language_models/src/provider/mistral.rs
@@ -1,4 +1,4 @@
-use anyhow::{anyhow, Result};
+use anyhow::{anyhow, Context as _, Result};
 use collections::BTreeMap;
 use editor::{Editor, EditorElement, EditorStyle};
 use futures::{future::BoxFuture, FutureExt, StreamExt};
@@ -7,8 +7,8 @@ use gpui::{
 };
 use http_client::HttpClient;
 use language_model::{
-    LanguageModel, LanguageModelCompletionEvent, LanguageModelId, LanguageModelName,
-    LanguageModelProvider, LanguageModelProviderId, LanguageModelProviderName,
+    AuthenticateError, LanguageModel, LanguageModelCompletionEvent, LanguageModelId,
+    LanguageModelName, LanguageModelProvider, LanguageModelProviderId, LanguageModelProviderName,
     LanguageModelProviderState, LanguageModelRequest, RateLimiter, Role,
 };
 
@@ -88,31 +88,36 @@ impl State {
         })
     }
 
-    fn authenticate(&self, cx: &mut Context<Self>) -> Task<Result<()>> {
+    fn authenticate(&self, cx: &mut Context<Self>) -> Task<Result<(), AuthenticateError>> {
         if self.is_authenticated() {
-            Task::ready(Ok(()))
-        } else {
-            let api_url = AllLanguageModelSettings::get_global(cx)
-                .mistral
-                .api_url
-                .clone();
-            cx.spawn(|this, mut cx| async move {
-                let (api_key, from_env) = if let Ok(api_key) = std::env::var(MISTRAL_API_KEY_VAR) {
-                    (api_key, true)
-                } else {
-                    let (_, api_key) = cx
-                        .update(|cx| cx.read_credentials(&api_url))?
-                        .await?
-                        .ok_or_else(|| anyhow!("credentials not found"))?;
-                    (String::from_utf8(api_key)?, false)
-                };
-                this.update(&mut cx, |this, cx| {
-                    this.api_key = Some(api_key);
-                    this.api_key_from_env = from_env;
-                    cx.notify();
-                })
-            })
+            return Task::ready(Ok(()));
         }
+
+        let api_url = AllLanguageModelSettings::get_global(cx)
+            .mistral
+            .api_url
+            .clone();
+        cx.spawn(|this, mut cx| async move {
+            let (api_key, from_env) = if let Ok(api_key) = std::env::var(MISTRAL_API_KEY_VAR) {
+                (api_key, true)
+            } else {
+                let (_, api_key) = cx
+                    .update(|cx| cx.read_credentials(&api_url))?
+                    .await?
+                    .ok_or(AuthenticateError::CredentialsNotFound)?;
+                (
+                    String::from_utf8(api_key).context("invalid {PROVIDER_NAME} API key")?,
+                    false,
+                )
+            };
+            this.update(&mut cx, |this, cx| {
+                this.api_key = Some(api_key);
+                this.api_key_from_env = from_env;
+                cx.notify();
+            })?;
+
+            Ok(())
+        })
     }
 }
 
@@ -196,7 +201,7 @@ impl LanguageModelProvider for MistralLanguageModelProvider {
         self.state.read(cx).is_authenticated()
     }
 
-    fn authenticate(&self, cx: &mut App) -> Task<Result<()>> {
+    fn authenticate(&self, cx: &mut App) -> Task<Result<(), AuthenticateError>> {
         self.state.update(cx, |state, cx| state.authenticate(cx))
     }
 
diff --git a/crates/language_models/src/provider/ollama.rs b/crates/language_models/src/provider/ollama.rs
index a1acf5b695..a982eb3aa7 100644
--- a/crates/language_models/src/provider/ollama.rs
+++ b/crates/language_models/src/provider/ollama.rs
@@ -2,7 +2,7 @@ use anyhow::{anyhow, bail, Result};
 use futures::{future::BoxFuture, stream::BoxStream, FutureExt, StreamExt};
 use gpui::{AnyView, App, AsyncApp, Context, Subscription, Task};
 use http_client::HttpClient;
-use language_model::LanguageModelCompletionEvent;
+use language_model::{AuthenticateError, LanguageModelCompletionEvent};
 use language_model::{
     LanguageModel, LanguageModelId, LanguageModelName, LanguageModelProvider,
     LanguageModelProviderId, LanguageModelProviderName, LanguageModelProviderState,
@@ -95,12 +95,13 @@ impl State {
         self.fetch_model_task.replace(task);
     }
 
-    fn authenticate(&mut self, cx: &mut Context<Self>) -> Task<Result<()>> {
+    fn authenticate(&mut self, cx: &mut Context<Self>) -> Task<Result<(), AuthenticateError>> {
         if self.is_authenticated() {
-            Task::ready(Ok(()))
-        } else {
-            self.fetch_models(cx)
+            return Task::ready(Ok(()));
         }
+
+        let fetch_models_task = self.fetch_models(cx);
+        cx.spawn(|_this, _cx| async move { Ok(fetch_models_task.await?) })
     }
 }
 
@@ -207,7 +208,7 @@ impl LanguageModelProvider for OllamaLanguageModelProvider {
         self.state.read(cx).is_authenticated()
     }
 
-    fn authenticate(&self, cx: &mut App) -> Task<Result<()>> {
+    fn authenticate(&self, cx: &mut App) -> Task<Result<(), AuthenticateError>> {
         self.state.update(cx, |state, cx| state.authenticate(cx))
     }
 
diff --git a/crates/language_models/src/provider/open_ai.rs b/crates/language_models/src/provider/open_ai.rs
index f47ccc2eca..765eae9b15 100644
--- a/crates/language_models/src/provider/open_ai.rs
+++ b/crates/language_models/src/provider/open_ai.rs
@@ -1,4 +1,4 @@
-use anyhow::{anyhow, Result};
+use anyhow::{anyhow, Context as _, Result};
 use collections::BTreeMap;
 use editor::{Editor, EditorElement, EditorStyle};
 use futures::{future::BoxFuture, FutureExt, StreamExt};
@@ -7,8 +7,8 @@ use gpui::{
 };
 use http_client::HttpClient;
 use language_model::{
-    LanguageModel, LanguageModelCompletionEvent, LanguageModelId, LanguageModelName,
-    LanguageModelProvider, LanguageModelProviderId, LanguageModelProviderName,
+    AuthenticateError, LanguageModel, LanguageModelCompletionEvent, LanguageModelId,
+    LanguageModelName, LanguageModelProvider, LanguageModelProviderId, LanguageModelProviderName,
     LanguageModelProviderState, LanguageModelRequest, RateLimiter, Role,
 };
 use open_ai::{
@@ -89,31 +89,36 @@ impl State {
         })
     }
 
-    fn authenticate(&self, cx: &mut Context<Self>) -> Task<Result<()>> {
+    fn authenticate(&self, cx: &mut Context<Self>) -> Task<Result<(), AuthenticateError>> {
         if self.is_authenticated() {
-            Task::ready(Ok(()))
-        } else {
-            let api_url = AllLanguageModelSettings::get_global(cx)
-                .openai
-                .api_url
-                .clone();
-            cx.spawn(|this, mut cx| async move {
-                let (api_key, from_env) = if let Ok(api_key) = std::env::var(OPENAI_API_KEY_VAR) {
-                    (api_key, true)
-                } else {
-                    let (_, api_key) = cx
-                        .update(|cx| cx.read_credentials(&api_url))?
-                        .await?
-                        .ok_or_else(|| anyhow!("credentials not found"))?;
-                    (String::from_utf8(api_key)?, false)
-                };
-                this.update(&mut cx, |this, cx| {
-                    this.api_key = Some(api_key);
-                    this.api_key_from_env = from_env;
-                    cx.notify();
-                })
-            })
+            return Task::ready(Ok(()));
         }
+
+        let api_url = AllLanguageModelSettings::get_global(cx)
+            .openai
+            .api_url
+            .clone();
+        cx.spawn(|this, mut cx| async move {
+            let (api_key, from_env) = if let Ok(api_key) = std::env::var(OPENAI_API_KEY_VAR) {
+                (api_key, true)
+            } else {
+                let (_, api_key) = cx
+                    .update(|cx| cx.read_credentials(&api_url))?
+                    .await?
+                    .ok_or(AuthenticateError::CredentialsNotFound)?;
+                (
+                    String::from_utf8(api_key).context("invalid {PROVIDER_NAME} API key")?,
+                    false,
+                )
+            };
+            this.update(&mut cx, |this, cx| {
+                this.api_key = Some(api_key);
+                this.api_key_from_env = from_env;
+                cx.notify();
+            })?;
+
+            Ok(())
+        })
     }
 }
 
@@ -197,7 +202,7 @@ impl LanguageModelProvider for OpenAiLanguageModelProvider {
         self.state.read(cx).is_authenticated()
     }
 
-    fn authenticate(&self, cx: &mut App) -> Task<Result<()>> {
+    fn authenticate(&self, cx: &mut App) -> Task<Result<(), AuthenticateError>> {
         self.state.update(cx, |state, cx| state.authenticate(cx))
     }