diff --git a/crates-tauri/yaak-app/src/lib.rs b/crates-tauri/yaak-app/src/lib.rs
index a1d89afa..0f2c465f 100644
--- a/crates-tauri/yaak-app/src/lib.rs
+++ b/crates-tauri/yaak-app/src/lib.rs
@@ -7,7 +7,7 @@ use crate::http_request::{resolve_http_request, send_http_request};
 use crate::import::import_data;
 use crate::models_ext::{BlobManagerExt, QueryManagerExt};
 use crate::notifications::YaakNotifier;
-use crate::render::{render_grpc_request, render_template};
+use crate::render::{render_grpc_request, render_json_value, render_template};
 use crate::updates::{UpdateMode, UpdateTrigger, YaakUpdater};
 use crate::uri_scheme::handle_deep_link;
 use error::Result as YaakResult;
@@ -1057,14 +1057,54 @@ async fn cmd_get_http_authentication_summaries<R: Runtime>(
 #[tauri::command]
 async fn cmd_get_http_authentication_config<R: Runtime>(
     window: WebviewWindow<R>,
+    app_handle: AppHandle<R>,
     plugin_manager: State<'_, PluginManager>,
+    encryption_manager: State<'_, EncryptionManager>,
     auth_name: &str,
     values: HashMap<String, JsonPrimitive>,
     model: AnyModel,
-    _environment_id: Option<&str>,
+    environment_id: Option<&str>,
 ) -> YaakResult<GetHttpAuthenticationConfigResponse> {
+    // Extract workspace_id and folder_id from the model to resolve the environment chain
+    let (workspace_id, folder_id) = match &model {
+        AnyModel::HttpRequest(r) => (r.workspace_id.clone(), r.folder_id.clone()),
+        AnyModel::GrpcRequest(r) => (r.workspace_id.clone(), r.folder_id.clone()),
+        AnyModel::WebsocketRequest(r) => (r.workspace_id.clone(), r.folder_id.clone()),
+        AnyModel::Folder(f) => (f.workspace_id.clone(), f.folder_id.clone()),
+        AnyModel::Workspace(w) => (w.id.clone(), None),
+        _ => return Err(GenericError("Unsupported model type for authentication config".into())),
+    };
+
+    // Resolve environment chain and render the values for token lookup
+    let environment_chain = app_handle.db().resolve_environments(
+        &workspace_id,
+        folder_id.as_deref(),
+        environment_id,
+    )?;
+    let plugin_manager_arc = Arc::new((*plugin_manager).clone());
+    let encryption_manager_arc = Arc::new((*encryption_manager).clone());
+    let cb = PluginTemplateCallback::new(
+        plugin_manager_arc,
+        encryption_manager_arc,
+        &window.plugin_context(),
+        RenderPurpose::Preview,
+    );
+
+    // Convert HashMap<String, JsonPrimitive> to serde_json::Value for rendering
+    let values_json: serde_json::Value = serde_json::to_value(&values)?;
+    let rendered_json =
+        render_json_value(values_json, environment_chain, &cb, &RenderOptions::throw()).await?;
+
+    // Convert back to HashMap<String, JsonPrimitive>
+    let rendered_values: HashMap<String, JsonPrimitive> = serde_json::from_value(rendered_json)?;
+
     Ok(plugin_manager
-        .get_http_authentication_config(&window.plugin_context(), auth_name, values, model.id())
+        .get_http_authentication_config(
+            &window.plugin_context(),
+            auth_name,
+            rendered_values,
+            model.id(),
+        )
         .await?)
 }
 
@@ -1111,19 +1151,54 @@ async fn cmd_call_grpc_request_action<R: Runtime>(
 #[tauri::command]
 async fn cmd_call_http_authentication_action<R: Runtime>(
     window: WebviewWindow<R>,
+    app_handle: AppHandle<R>,
     plugin_manager: State<'_, PluginManager>,
+    encryption_manager: State<'_, EncryptionManager>,
     auth_name: &str,
     action_index: i32,
     values: HashMap<String, JsonPrimitive>,
     model: AnyModel,
-    _environment_id: Option<&str>,
+    environment_id: Option<&str>,
 ) -> YaakResult<()> {
+    // Extract workspace_id and folder_id from the model to resolve the environment chain
+    let (workspace_id, folder_id) = match &model {
+        AnyModel::HttpRequest(r) => (r.workspace_id.clone(), r.folder_id.clone()),
+        AnyModel::GrpcRequest(r) => (r.workspace_id.clone(), r.folder_id.clone()),
+        AnyModel::WebsocketRequest(r) => (r.workspace_id.clone(), r.folder_id.clone()),
+        AnyModel::Folder(f) => (f.workspace_id.clone(), f.folder_id.clone()),
+        AnyModel::Workspace(w) => (w.id.clone(), None),
+        _ => return Err(GenericError("Unsupported model type for authentication action".into())),
+    };
+
+    // Resolve environment chain and render the values
+    let environment_chain = app_handle.db().resolve_environments(
+        &workspace_id,
+        folder_id.as_deref(),
+        environment_id,
+    )?;
+    let plugin_manager_arc = Arc::new((*plugin_manager).clone());
+    let encryption_manager_arc = Arc::new((*encryption_manager).clone());
+    let cb = PluginTemplateCallback::new(
+        plugin_manager_arc,
+        encryption_manager_arc,
+        &window.plugin_context(),
+        RenderPurpose::Send,
+    );
+
+    // Convert HashMap<String, JsonPrimitive> to serde_json::Value for rendering
+    let values_json: serde_json::Value = serde_json::to_value(&values)?;
+    let rendered_json =
+        render_json_value(values_json, environment_chain, &cb, &RenderOptions::throw()).await?;
+
+    // Convert back to HashMap<String, JsonPrimitive>
+    let rendered_values: HashMap<String, JsonPrimitive> = serde_json::from_value(rendered_json)?;
+
     Ok(plugin_manager
         .call_http_authentication_action(
             &window.plugin_context(),
             auth_name,
             action_index,
-            values,
+            rendered_values,
             &model.id(),
         )
         .await?)
diff --git a/packages/plugin-runtime-types/src/bindings/gen_models.ts b/packages/plugin-runtime-types/src/bindings/gen_models.ts
index 87c32f40..1963f828 100644
--- a/packages/plugin-runtime-types/src/bindings/gen_models.ts
+++ b/packages/plugin-runtime-types/src/bindings/gen_models.ts
@@ -12,6 +12,8 @@ export type CookieExpires = { "AtUtc": string } | "SessionEnd";
 
 export type CookieJar = { model: "cookie_jar", id: string, createdAt: string, updatedAt: string, workspaceId: string, cookies: Array<Cookie>, name: string, };
 
+export type DnsOverride = { hostname: string, ipv4: Array<string>, ipv6: Array<string>, enabled?: boolean, };
+
 export type EditorKeymap = "default" | "vim" | "vscode" | "emacs";
 
 export type EncryptedKey = { encryptedKey: string, };
@@ -77,6 +79,6 @@ export type WebsocketEventType = "binary" | "close" | "frame" | "open" | "ping"
 
 export type WebsocketRequest = { model: "websocket_request", id: string, createdAt: string, updatedAt: string, workspaceId: string, folderId: string | null, authentication: Record<string, any>, authenticationType: string | null, description: string, headers: Array<HttpRequestHeader>, message: string, name: string, sortPriority: number, url: string, urlParameters: Array<HttpUrlParameter>, };
 
-export type Workspace = { model: "workspace", id: string, createdAt: string, updatedAt: string, authentication: Record<string, any>, authenticationType: string | null, description: string, headers: Array<HttpRequestHeader>, name: string, encryptionKeyChallenge: string | null, settingValidateCertificates: boolean, settingFollowRedirects: boolean, settingRequestTimeout: number, };
+export type Workspace = { model: "workspace", id: string, createdAt: string, updatedAt: string, authentication: Record<string, any>, authenticationType: string | null, description: string, headers: Array<HttpRequestHeader>, name: string, encryptionKeyChallenge: string | null, settingValidateCertificates: boolean, settingFollowRedirects: boolean, settingRequestTimeout: number, settingDnsOverrides: Array<DnsOverride>, };
 
 export type WorkspaceMeta = { model: "workspace_meta", id: string, workspaceId: string, createdAt: string, updatedAt: string, encryptionKey: EncryptedKey | null, settingSyncDir: string | null, };