diff --git a/crates/goose-server/src/openapi.rs b/crates/goose-server/src/openapi.rs
index ae8bc4d5..46b7f2d9 100644
--- a/crates/goose-server/src/openapi.rs
+++ b/crates/goose-server/src/openapi.rs
@@ -21,6 +21,7 @@ use utoipa::OpenApi;
         super::routes::config_management::get_extensions,
         super::routes::config_management::read_all_config,
         super::routes::config_management::providers,
+        super::routes::config_management::upsert_permissions,
         super::routes::agent::get_tools,
     ),
     components(schemas(
@@ -31,6 +32,8 @@ use utoipa::OpenApi;
         super::routes::config_management::ProviderDetails,
         super::routes::config_management::ExtensionResponse,
         super::routes::config_management::ExtensionQuery,
+        super::routes::config_management::ToolPermission,
+        super::routes::config_management::UpsertPermissionsQuery,
         ProviderMetadata,
         ExtensionEntry,
         ExtensionConfig,
diff --git a/crates/goose-server/src/routes/agent.rs b/crates/goose-server/src/routes/agent.rs
index bf758cfc..011d9c87 100644
--- a/crates/goose-server/src/routes/agent.rs
+++ b/crates/goose-server/src/routes/agent.rs
@@ -5,10 +5,13 @@ use axum::{
     routing::{get, post},
     Json, Router,
 };
-use goose::agents::{extension::ToolInfo, extension_manager::get_parameter_names};
 use goose::config::Config;
 use goose::config::PermissionManager;
 use goose::{agents::Agent, model::ModelConfig, providers};
+use goose::{
+    agents::{extension::ToolInfo, extension_manager::get_parameter_names},
+    config::permission::PermissionLevel,
+};
 use serde::{Deserialize, Serialize};
 use std::collections::HashMap;
 use std::env;
@@ -173,7 +176,7 @@ async fn list_providers() -> Json<Vec<ProviderList>> {
         ("extension_name" = Option<String>, Query, description = "Optional extension name to filter tools")
     ),
     responses(
-        (status = 200, description = "Tools retrieved successfully", body = Vec<Tool>),
+        (status = 200, description = "Tools retrieved successfully", body = Vec<ToolInfo>),
         (status = 401, description = "Unauthorized - invalid secret key"),
         (status = 424, description = "Agent not initialized"),
         (status = 500, description = "Internal server error")
@@ -193,11 +196,13 @@ async fn get_tools(
         return Err(StatusCode::UNAUTHORIZED);
     }
 
+    let config = Config::global();
+    let goose_mode = config.get_param("GOOSE_MODE").unwrap_or("auto".to_string());
     let mut agent = state.agent.write().await;
     let agent = agent.as_mut().ok_or(StatusCode::PRECONDITION_REQUIRED)?;
     let permission_manager = PermissionManager::default();
 
-    let tools = agent
+    let mut tools: Vec<ToolInfo> = agent
         .list_tools()
         .await
         .into_iter()
@@ -210,14 +215,27 @@ async fn get_tools(
             }
         })
         .map(|tool| {
+            let permission = permission_manager
+                .get_user_permission(&tool.name)
+                .or_else(|| {
+                    if goose_mode == "smart_approve" {
+                        permission_manager.get_smart_approve_permission(&tool.name)
+                    } else if goose_mode == "approve" {
+                        Some(PermissionLevel::AskBefore)
+                    } else {
+                        None
+                    }
+                });
+
             ToolInfo::new(
                 &tool.name,
                 &tool.description,
                 get_parameter_names(&tool),
-                permission_manager.get_user_permission(&tool.name),
+                permission,
             )
         })
-        .collect();
+        .collect::<Vec<ToolInfo>>();
+    tools.sort_by(|a, b| a.name.cmp(&b.name));
 
     Ok(Json(tools))
 }
diff --git a/crates/goose-server/src/routes/config_management.rs b/crates/goose-server/src/routes/config_management.rs
index 3b06dc5d..bb09a2e5 100644
--- a/crates/goose-server/src/routes/config_management.rs
+++ b/crates/goose-server/src/routes/config_management.rs
@@ -5,12 +5,12 @@ use axum::{
     routing::{delete, get, post},
     Json, Router,
 };
-use goose::agents::ExtensionConfig;
-use goose::config::extensions::name_to_key;
 use goose::config::Config;
+use goose::config::{extensions::name_to_key, PermissionManager};
 use goose::config::{ExtensionConfigManager, ExtensionEntry};
 use goose::providers::base::ProviderMetadata;
 use goose::providers::providers as get_providers;
+use goose::{agents::ExtensionConfig, config::permission::PermissionLevel};
 use http::{HeaderMap, StatusCode};
 use serde::{Deserialize, Serialize};
 use serde_json::Value;
@@ -78,6 +78,18 @@ pub struct ProvidersResponse {
     pub providers: Vec<ProviderDetails>,
 }
 
+#[derive(Debug, Serialize, Deserialize, ToSchema)]
+pub struct ToolPermission {
+    /// Unique identifier and name of the tool, format <extension_name>__<tool_name>
+    pub tool_name: String,
+    pub permission: PermissionLevel,
+}
+
+#[derive(Deserialize, ToSchema)]
+pub struct UpsertPermissionsQuery {
+    pub tool_permissions: Vec<ToolPermission>,
+}
+
 #[utoipa::path(
     post,
     path = "/config/upsert",
@@ -389,6 +401,34 @@ pub async fn init_config(
     }
 }
 
+#[utoipa::path(
+    post,
+    path = "/config/permissions",
+    request_body = UpsertPermissionsQuery,
+    responses(
+        (status = 200, description = "Permission update completed", body = String),
+        (status = 400, description = "Invalid request"),
+    )
+)]
+pub async fn upsert_permissions(
+    State(state): State<AppState>,
+    headers: HeaderMap,
+    Json(query): Json<UpsertPermissionsQuery>,
+) -> Result<Json<String>, StatusCode> {
+    verify_secret_key(&headers, &state)?;
+
+    let mut permission_manager = PermissionManager::default();
+    // Iterate over each tool permission and update permissions
+    for tool_permission in &query.tool_permissions {
+        permission_manager.update_user_permission(
+            &tool_permission.tool_name,
+            tool_permission.permission.clone(),
+        );
+    }
+
+    Ok(Json("Permissions updated successfully".to_string()))
+}
+
 pub fn routes(state: AppState) -> Router {
     Router::new()
         .route("/config", get(read_all_config))
@@ -400,5 +440,6 @@ pub fn routes(state: AppState) -> Router {
         .route("/config/extensions/:name", delete(remove_extension))
         .route("/config/providers", get(providers))
         .route("/config/init", post(init_config))
+        .route("/config/permissions", post(upsert_permissions))
         .with_state(state)
 }
diff --git a/crates/goose-server/src/routes/reply.rs b/crates/goose-server/src/routes/reply.rs
index da3e0e05..9f115dca 100644
--- a/crates/goose-server/src/routes/reply.rs
+++ b/crates/goose-server/src/routes/reply.rs
@@ -368,7 +368,7 @@ async fn ask_handler(
 #[derive(Debug, Deserialize)]
 struct ToolConfirmationRequest {
     id: String,
-    confirmed: bool,
+    action: String,
 }
 
 async fn confirm_handler(
@@ -389,11 +389,14 @@ async fn confirm_handler(
     let agent = state.agent.clone();
     let agent = agent.read().await;
     let agent = agent.as_ref().ok_or(StatusCode::NOT_FOUND)?;
-    let permission = if request.confirmed {
-        Permission::AllowOnce
-    } else {
-        Permission::DenyOnce
+
+    let permission = match request.action.as_str() {
+        "always_allow" => Permission::AlwaysAllow,
+        "allow_once" => Permission::AllowOnce,
+        "deny" => Permission::DenyOnce,
+        _ => Permission::DenyOnce,
     };
+
     agent
         .handle_confirmation(
             request.id.clone(),
diff --git a/crates/goose/src/agents/extension.rs b/crates/goose/src/agents/extension.rs
index 1375b776..dbbea2d0 100644
--- a/crates/goose/src/agents/extension.rs
+++ b/crates/goose/src/agents/extension.rs
@@ -24,6 +24,8 @@ pub enum ExtensionError {
     Transport(#[from] mcp_client::transport::Error),
     #[error("Environment variable `{0}` is not allowed to be overridden.")]
     InvalidEnvVar(String),
+    #[error("Join error occurred during task execution: {0}")]
+    TaskJoinError(#[from] tokio::task::JoinError),
 }
 
 pub type ExtensionResult<T> = Result<T, ExtensionError>;
diff --git a/crates/goose/src/agents/extension_manager.rs b/crates/goose/src/agents/extension_manager.rs
index 5694840c..14aab739 100644
--- a/crates/goose/src/agents/extension_manager.rs
+++ b/crates/goose/src/agents/extension_manager.rs
@@ -1,5 +1,6 @@
 use anyhow::Result;
 use chrono::{DateTime, TimeZone, Utc};
+use futures::future;
 use futures::stream::{FuturesUnordered, StreamExt};
 use mcp_client::McpService;
 use mcp_core::protocol::GetPromptResult;
@@ -8,6 +9,7 @@ use std::sync::Arc;
 use std::sync::LazyLock;
 use std::time::Duration;
 use tokio::sync::Mutex;
+use tokio::task;
 use tracing::debug;
 
 use super::extension::{ExtensionConfig, ExtensionError, ExtensionInfo, ExtensionResult, ToolInfo};
@@ -230,29 +232,47 @@ impl ExtensionManager {
 
     /// Get all tools from all clients with proper prefixing
     pub async fn get_prefixed_tools(&self) -> ExtensionResult<Vec<Tool>> {
+        let client_futures = self.clients.iter().map(|(name, client)| {
+            let name = name.clone();
+            let client = client.clone();
+
+            task::spawn(async move {
+                let mut tools = Vec::new();
+                let client_guard = client.lock().await;
+                let mut client_tools = client_guard.list_tools(None).await?;
+
+                loop {
+                    for tool in client_tools.tools {
+                        tools.push(Tool::new(
+                            format!("{}__{}", name, tool.name),
+                            &tool.description,
+                            tool.input_schema,
+                            tool.annotations,
+                        ));
+                    }
+
+                    // Exit loop when there are no more pages
+                    if client_tools.next_cursor.is_none() {
+                        break;
+                    }
+
+                    client_tools = client_guard.list_tools(client_tools.next_cursor).await?;
+                }
+
+                Ok::<Vec<Tool>, ExtensionError>(tools)
+            })
+        });
+
+        // Collect all results concurrently
+        let results = future::join_all(client_futures).await;
+
+        // Aggregate tools and handle errors
         let mut tools = Vec::new();
-
-        // Add tools from MCP extensions with prefixing
-        for (name, client) in &self.clients {
-            let client_guard = client.lock().await;
-            let mut client_tools = client_guard.list_tools(None).await?;
-
-            loop {
-                for tool in client_tools.tools {
-                    tools.push(Tool::new(
-                        format!("{}__{}", name, tool.name),
-                        &tool.description,
-                        tool.input_schema,
-                        tool.annotations,
-                    ));
-                }
-
-                // exit loop when there are no more pages
-                if client_tools.next_cursor.is_none() {
-                    break;
-                }
-
-                client_tools = client_guard.list_tools(client_tools.next_cursor).await?;
+        for result in results {
+            match result {
+                Ok(Ok(client_tools)) => tools.extend(client_tools),
+                Ok(Err(err)) => return Err(err),
+                Err(join_err) => return Err(ExtensionError::from(join_err)),
             }
         }
 
diff --git a/ui/desktop/openapi.json b/ui/desktop/openapi.json
index 8a2d6c88..f384d068 100644
--- a/ui/desktop/openapi.json
+++ b/ui/desktop/openapi.json
@@ -39,7 +39,7 @@
                 "schema": {
                   "type": "array",
                   "items": {
-                    "$ref": "#/components/schemas/Tool"
+                    "$ref": "#/components/schemas/ToolInfo"
                   }
                 }
               }
@@ -196,6 +196,39 @@
         }
       }
     },
+    "/config/permissions": {
+      "post": {
+        "tags": [
+          "super::routes::config_management"
+        ],
+        "operationId": "upsert_permissions",
+        "requestBody": {
+          "content": {
+            "application/json": {
+              "schema": {
+                "$ref": "#/components/schemas/UpsertPermissionsQuery"
+              }
+            }
+          },
+          "required": true
+        },
+        "responses": {
+          "200": {
+            "description": "Permission update completed",
+            "content": {
+              "text/plain": {
+                "schema": {
+                  "type": "string"
+                }
+              }
+            }
+          },
+          "400": {
+            "description": "Invalid request"
+          }
+        }
+      }
+    },
     "/config/providers": {
       "get": {
         "tags": [
@@ -783,6 +816,22 @@
           }
         }
       },
+      "ToolPermission": {
+        "type": "object",
+        "required": [
+          "tool_name",
+          "permission"
+        ],
+        "properties": {
+          "permission": {
+            "$ref": "#/components/schemas/PermissionLevel"
+          },
+          "tool_name": {
+            "type": "string",
+            "description": "Unique identifier and name of the tool, format <extension_name>__<tool_name>"
+          }
+        }
+      },
       "UpsertConfigQuery": {
         "type": "object",
         "required": [
@@ -799,6 +848,20 @@
           },
           "value": {}
         }
+      },
+      "UpsertPermissionsQuery": {
+        "type": "object",
+        "required": [
+          "tool_permissions"
+        ],
+        "properties": {
+          "tool_permissions": {
+            "type": "array",
+            "items": {
+              "$ref": "#/components/schemas/ToolPermission"
+            }
+          }
+        }
       }
     }
   }
diff --git a/ui/desktop/package-lock.json b/ui/desktop/package-lock.json
index 32d07886..62933576 100644
--- a/ui/desktop/package-lock.json
+++ b/ui/desktop/package-lock.json
@@ -14,12 +14,12 @@
         "@hey-api/client-fetch": "^0.8.1",
         "@radix-ui/react-accordion": "^1.2.2",
         "@radix-ui/react-avatar": "^1.1.1",
-        "@radix-ui/react-dialog": "^1.1.4",
+        "@radix-ui/react-dialog": "^1.1.7",
         "@radix-ui/react-icons": "^1.3.1",
         "@radix-ui/react-popover": "^1.1.6",
         "@radix-ui/react-radio-group": "^1.2.3",
         "@radix-ui/react-scroll-area": "^1.2.0",
-        "@radix-ui/react-select": "^2.1.5",
+        "@radix-ui/react-select": "^2.1.7",
         "@radix-ui/react-slot": "^1.1.1",
         "@radix-ui/react-tabs": "^1.1.1",
         "@radix-ui/themes": "^3.1.5",
@@ -600,26 +600,26 @@
       }
     },
     "node_modules/@babel/helpers": {
-      "version": "7.26.7",
-      "resolved": "https://registry.npmjs.org/@babel/helpers/-/helpers-7.26.7.tgz",
-      "integrity": "sha512-8NHiL98vsi0mbPQmYAGWwfcFaOy4j2HY49fXJCfuDcdE7fMIsH9a7GdaeXpIBsbT7307WU8KCMp5pUVDNL4f9A==",
+      "version": "7.27.0",
+      "resolved": "https://registry.npmjs.org/@babel/helpers/-/helpers-7.27.0.tgz",
+      "integrity": "sha512-U5eyP/CTFPuNE3qk+WZMxFkp/4zUzdceQlfzf7DdGdhp+Fezd7HD+i8Y24ZuTMKX3wQBld449jijbGq6OdGNQg==",
       "dev": true,
       "license": "MIT",
       "dependencies": {
-        "@babel/template": "^7.25.9",
-        "@babel/types": "^7.26.7"
+        "@babel/template": "^7.27.0",
+        "@babel/types": "^7.27.0"
       },
       "engines": {
         "node": ">=6.9.0"
       }
     },
     "node_modules/@babel/parser": {
-      "version": "7.26.8",
-      "resolved": "https://registry.npmjs.org/@babel/parser/-/parser-7.26.8.tgz",
-      "integrity": "sha512-TZIQ25pkSoaKEYYaHbbxkfL36GNsQ6iFiBbeuzAkLnXayKR1yP1zFe+NxuZWWsUyvt8icPU9CCq0sgWGXR1GEw==",
+      "version": "7.27.0",
+      "resolved": "https://registry.npmjs.org/@babel/parser/-/parser-7.27.0.tgz",
+      "integrity": "sha512-iaepho73/2Pz7w2eMS0Q5f83+0RKI7i4xmiYeBmDzfRVbQtTOG7Ts0S4HzJVsTMGI9keU8rNfuZr8DKfSt7Yyg==",
       "license": "MIT",
       "dependencies": {
-        "@babel/types": "^7.26.8"
+        "@babel/types": "^7.27.0"
       },
       "bin": {
         "parser": "bin/babel-parser.js"
@@ -673,14 +673,14 @@
       }
     },
     "node_modules/@babel/template": {
-      "version": "7.26.8",
-      "resolved": "https://registry.npmjs.org/@babel/template/-/template-7.26.8.tgz",
-      "integrity": "sha512-iNKaX3ZebKIsCvJ+0jd6embf+Aulaa3vNBqZ41kM7iTWjx5qzWKXGHiJUW3+nTpQ18SG11hdF8OAzKrpXkb96Q==",
+      "version": "7.27.0",
+      "resolved": "https://registry.npmjs.org/@babel/template/-/template-7.27.0.tgz",
+      "integrity": "sha512-2ncevenBqXI6qRMukPlXwHKHchC7RyMuu4xv5JBXRfOGVcTy1mXCD12qrp7Jsoxll1EV3+9sE4GugBVRjT2jFA==",
       "license": "MIT",
       "dependencies": {
         "@babel/code-frame": "^7.26.2",
-        "@babel/parser": "^7.26.8",
-        "@babel/types": "^7.26.8"
+        "@babel/parser": "^7.27.0",
+        "@babel/types": "^7.27.0"
       },
       "engines": {
         "node": ">=6.9.0"
@@ -705,9 +705,9 @@
       }
     },
     "node_modules/@babel/types": {
-      "version": "7.26.8",
-      "resolved": "https://registry.npmjs.org/@babel/types/-/types-7.26.8.tgz",
-      "integrity": "sha512-eUuWapzEGWFEpHFxgEaBG8e3n6S8L3MSu0oda755rOfabWPnh0Our1AozNFVUxGFIhbKgd1ksprsoDGMinTOTA==",
+      "version": "7.27.0",
+      "resolved": "https://registry.npmjs.org/@babel/types/-/types-7.27.0.tgz",
+      "integrity": "sha512-H45s8fVLYjbhFH62dIJ3WtmJ6RSPt/3DRO0ZcT2SUiYiQyz3BLVb9ADEnLl91m74aQPS3AzzeajZHYOalWe3bg==",
       "license": "MIT",
       "dependencies": {
         "@babel/helper-string-parser": "^7.25.9",
@@ -2945,6 +2945,42 @@
         }
       }
     },
+    "node_modules/@radix-ui/react-alert-dialog/node_modules/@radix-ui/react-dialog": {
+      "version": "1.1.6",
+      "resolved": "https://registry.npmjs.org/@radix-ui/react-dialog/-/react-dialog-1.1.6.tgz",
+      "integrity": "sha512-/IVhJV5AceX620DUJ4uYVMymzsipdKBzo3edo+omeskCKGm9FRHM0ebIdbPnlQVJqyuHbuBltQUOG2mOTq2IYw==",
+      "license": "MIT",
+      "dependencies": {
+        "@radix-ui/primitive": "1.1.1",
+        "@radix-ui/react-compose-refs": "1.1.1",
+        "@radix-ui/react-context": "1.1.1",
+        "@radix-ui/react-dismissable-layer": "1.1.5",
+        "@radix-ui/react-focus-guards": "1.1.1",
+        "@radix-ui/react-focus-scope": "1.1.2",
+        "@radix-ui/react-id": "1.1.0",
+        "@radix-ui/react-portal": "1.1.4",
+        "@radix-ui/react-presence": "1.1.2",
+        "@radix-ui/react-primitive": "2.0.2",
+        "@radix-ui/react-slot": "1.1.2",
+        "@radix-ui/react-use-controllable-state": "1.1.0",
+        "aria-hidden": "^1.2.4",
+        "react-remove-scroll": "^2.6.3"
+      },
+      "peerDependencies": {
+        "@types/react": "*",
+        "@types/react-dom": "*",
+        "react": "^16.8 || ^17.0 || ^18.0 || ^19.0 || ^19.0.0-rc",
+        "react-dom": "^16.8 || ^17.0 || ^18.0 || ^19.0 || ^19.0.0-rc"
+      },
+      "peerDependenciesMeta": {
+        "@types/react": {
+          "optional": true
+        },
+        "@types/react-dom": {
+          "optional": true
+        }
+      }
+    },
     "node_modules/@radix-ui/react-arrow": {
       "version": "1.1.2",
       "resolved": "https://registry.npmjs.org/@radix-ui/react-arrow/-/react-arrow-1.1.2.tgz",
@@ -3162,23 +3198,23 @@
       }
     },
     "node_modules/@radix-ui/react-dialog": {
-      "version": "1.1.6",
-      "resolved": "https://registry.npmjs.org/@radix-ui/react-dialog/-/react-dialog-1.1.6.tgz",
-      "integrity": "sha512-/IVhJV5AceX620DUJ4uYVMymzsipdKBzo3edo+omeskCKGm9FRHM0ebIdbPnlQVJqyuHbuBltQUOG2mOTq2IYw==",
+      "version": "1.1.7",
+      "resolved": "https://registry.npmjs.org/@radix-ui/react-dialog/-/react-dialog-1.1.7.tgz",
+      "integrity": "sha512-EIdma8C0C/I6kL6sO02avaCRqi3fmWJpxH6mqbVScorW6nNktzKJT/le7VPho3o/7wCsyRg3z0+Q+Obr0Gy/VQ==",
       "license": "MIT",
       "dependencies": {
-        "@radix-ui/primitive": "1.1.1",
-        "@radix-ui/react-compose-refs": "1.1.1",
-        "@radix-ui/react-context": "1.1.1",
-        "@radix-ui/react-dismissable-layer": "1.1.5",
-        "@radix-ui/react-focus-guards": "1.1.1",
-        "@radix-ui/react-focus-scope": "1.1.2",
-        "@radix-ui/react-id": "1.1.0",
-        "@radix-ui/react-portal": "1.1.4",
-        "@radix-ui/react-presence": "1.1.2",
-        "@radix-ui/react-primitive": "2.0.2",
-        "@radix-ui/react-slot": "1.1.2",
-        "@radix-ui/react-use-controllable-state": "1.1.0",
+        "@radix-ui/primitive": "1.1.2",
+        "@radix-ui/react-compose-refs": "1.1.2",
+        "@radix-ui/react-context": "1.1.2",
+        "@radix-ui/react-dismissable-layer": "1.1.6",
+        "@radix-ui/react-focus-guards": "1.1.2",
+        "@radix-ui/react-focus-scope": "1.1.3",
+        "@radix-ui/react-id": "1.1.1",
+        "@radix-ui/react-portal": "1.1.5",
+        "@radix-ui/react-presence": "1.1.3",
+        "@radix-ui/react-primitive": "2.0.3",
+        "@radix-ui/react-slot": "1.2.0",
+        "@radix-ui/react-use-controllable-state": "1.1.1",
         "aria-hidden": "^1.2.4",
         "react-remove-scroll": "^2.6.3"
       },
@@ -3197,6 +3233,282 @@
         }
       }
     },
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+          "optional": true
+        },
+        "@types/react-dom": {
+          "optional": true
+        }
+      }
+    },
     "node_modules/range-parser": {
       "version": "1.2.1",
       "resolved": "https://registry.npmjs.org/range-parser/-/range-parser-1.2.1.tgz",
diff --git a/ui/desktop/package.json b/ui/desktop/package.json
index 9a868e8e..01f2afaf 100644
--- a/ui/desktop/package.json
+++ b/ui/desktop/package.json
@@ -82,12 +82,12 @@
     "@hey-api/client-fetch": "^0.8.1",
     "@radix-ui/react-accordion": "^1.2.2",
     "@radix-ui/react-avatar": "^1.1.1",
-    "@radix-ui/react-dialog": "^1.1.4",
+    "@radix-ui/react-dialog": "^1.1.7",
     "@radix-ui/react-icons": "^1.3.1",
     "@radix-ui/react-popover": "^1.1.6",
     "@radix-ui/react-radio-group": "^1.2.3",
     "@radix-ui/react-scroll-area": "^1.2.0",
-    "@radix-ui/react-select": "^2.1.5",
+    "@radix-ui/react-select": "^2.1.7",
     "@radix-ui/react-slot": "^1.1.1",
     "@radix-ui/react-tabs": "^1.1.1",
     "@radix-ui/themes": "^3.1.5",
diff --git a/ui/desktop/src/api/sdk.gen.ts b/ui/desktop/src/api/sdk.gen.ts
index 66010de1..239536df 100644
--- a/ui/desktop/src/api/sdk.gen.ts
+++ b/ui/desktop/src/api/sdk.gen.ts
@@ -1,7 +1,7 @@
 // This file is auto-generated by @hey-api/openapi-ts
 
 import type { Options as ClientOptions, TDataShape, Client } from '@hey-api/client-fetch';
-import type { GetToolsData, GetToolsResponse, ReadAllConfigData, ReadAllConfigResponse, GetExtensionsData, GetExtensionsResponse, AddExtensionData, AddExtensionResponse, RemoveExtensionData, RemoveExtensionResponse, InitConfigData, InitConfigResponse, ProvidersData, ProvidersResponse2, ReadConfigData, RemoveConfigData, RemoveConfigResponse, UpsertConfigData, UpsertConfigResponse } from './types.gen';
+import type { GetToolsData, GetToolsResponse, ReadAllConfigData, ReadAllConfigResponse, GetExtensionsData, GetExtensionsResponse, AddExtensionData, AddExtensionResponse, RemoveExtensionData, RemoveExtensionResponse, InitConfigData, InitConfigResponse, UpsertPermissionsData, UpsertPermissionsResponse, ProvidersData, ProvidersResponse2, ReadConfigData, RemoveConfigData, RemoveConfigResponse, UpsertConfigData, UpsertConfigResponse } from './types.gen';
 import { client as _heyApiClient } from './client.gen';
 
 export type Options<TData extends TDataShape = TDataShape, ThrowOnError extends boolean = boolean> = ClientOptions<TData, ThrowOnError> & {
@@ -64,6 +64,17 @@ export const initConfig = <ThrowOnError extends boolean = false>(options?: Optio
     });
 };
 
+export const upsertPermissions = <ThrowOnError extends boolean = false>(options: Options<UpsertPermissionsData, ThrowOnError>) => {
+    return (options.client ?? _heyApiClient).post<UpsertPermissionsResponse, unknown, ThrowOnError>({
+        url: '/config/permissions',
+        ...options,
+        headers: {
+            'Content-Type': 'application/json',
+            ...options?.headers
+        }
+    });
+};
+
 export const providers = <ThrowOnError extends boolean = false>(options?: Options<ProvidersData, ThrowOnError>) => {
     return (options?.client ?? _heyApiClient).get<ProvidersResponse2, unknown, ThrowOnError>({
         url: '/config/providers',
diff --git a/ui/desktop/src/api/types.gen.ts b/ui/desktop/src/api/types.gen.ts
index 32c21c87..0409a2e6 100644
--- a/ui/desktop/src/api/types.gen.ts
+++ b/ui/desktop/src/api/types.gen.ts
@@ -235,12 +235,24 @@ export type ToolInfo = {
     permission?: PermissionLevel | null;
 };
 
+export type ToolPermission = {
+    permission: PermissionLevel;
+    /**
+     * Unique identifier and name of the tool, format <extension_name>__<tool_name>
+     */
+    tool_name: string;
+};
+
 export type UpsertConfigQuery = {
     is_secret: boolean;
     key: string;
     value: unknown;
 };
 
+export type UpsertPermissionsQuery = {
+    tool_permissions: Array<ToolPermission>;
+};
+
 export type GetToolsData = {
     body?: never;
     path?: never;
@@ -272,7 +284,7 @@ export type GetToolsResponses = {
     /**
      * Tools retrieved successfully
      */
-    200: Array<Tool>;
+    200: Array<ToolInfo>;
 };
 
 export type GetToolsResponse = GetToolsResponses[keyof GetToolsResponses];
@@ -399,6 +411,29 @@ export type InitConfigResponses = {
 
 export type InitConfigResponse = InitConfigResponses[keyof InitConfigResponses];
 
+export type UpsertPermissionsData = {
+    body: UpsertPermissionsQuery;
+    path?: never;
+    query?: never;
+    url: '/config/permissions';
+};
+
+export type UpsertPermissionsErrors = {
+    /**
+     * Invalid request
+     */
+    400: unknown;
+};
+
+export type UpsertPermissionsResponses = {
+    /**
+     * Permission update completed
+     */
+    200: string;
+};
+
+export type UpsertPermissionsResponse = UpsertPermissionsResponses[keyof UpsertPermissionsResponses];
+
 export type ProvidersData = {
     body?: never;
     path?: never;
diff --git a/ui/desktop/src/components/ToolCallConfirmation.tsx b/ui/desktop/src/components/ToolCallConfirmation.tsx
index 7ea2181b..6b4d89b4 100644
--- a/ui/desktop/src/components/ToolCallConfirmation.tsx
+++ b/ui/desktop/src/components/ToolCallConfirmation.tsx
@@ -1,22 +1,53 @@
-import React, { useState } from 'react';
+import { useState } from 'react';
 import { ConfirmToolRequest } from '../utils/toolConfirm';
 import { snakeToTitleCase } from '../utils';
+import PermissionModal from './settings_v2/permission/PermissionModal';
+import { ChevronRight } from 'lucide-react';
+
+const ALWAYS_ALLOW = 'always_allow';
+const ALLOW_ONCE = 'allow_once';
+const DENY = 'deny';
+
+interface ToolConfirmationProps {
+  isCancelledMessage: boolean;
+  isClicked: boolean;
+  toolConfirmationId: string;
+  toolName: string;
+}
 
 export default function ToolConfirmation({
   isCancelledMessage,
   isClicked,
   toolConfirmationId,
   toolName,
-}) {
+}: ToolConfirmationProps) {
   const [clicked, setClicked] = useState(isClicked);
   const [status, setStatus] = useState('unknown');
+  const [actionDisplay, setActionDisplay] = useState('');
+  const [isModalOpen, setIsModalOpen] = useState(false);
 
-  const handleButtonClick = (confirmed) => {
+  const handleButtonClick = (action: string) => {
     setClicked(true);
-    setStatus(confirmed ? 'approved' : 'denied');
-    ConfirmToolRequest(toolConfirmationId, confirmed);
+    setStatus(action);
+    if (action === ALWAYS_ALLOW) {
+      setActionDisplay('always allowed');
+    } else if (action === ALLOW_ONCE) {
+      setActionDisplay('allowed once');
+    } else {
+      setActionDisplay('denied');
+    }
+    ConfirmToolRequest(toolConfirmationId, action);
   };
 
+  const handleModalClose = () => {
+    setIsModalOpen(false);
+  };
+
+  function getExtensionName(toolName: string): string {
+    const parts = toolName.split('__');
+    return parts.length > 1 ? parts[0] : '';
+  }
+
   return isCancelledMessage ? (
     <div className="goose-message-content bg-bgSubtle rounded-2xl px-4 py-2 text-textStandard">
       Tool call confirmation is cancelled.
@@ -27,9 +58,9 @@ export default function ToolConfirmation({
         Goose would like to call the above tool. Allow?
       </div>
       {clicked ? (
-        <div className="goose-message-tool bg-bgApp border border-borderSubtle dark:border-gray-700 rounded-b-2xl px-4 pt-4 pb-2 flex gap-4 mt-1">
+        <div className="goose-message-tool bg-bgApp border border-borderSubtle dark:border-gray-700 rounded-b-2xl px-4 pt-2 pb-2 flex items-center justify-between">
           <div className="flex items-center">
-            {status === 'approved' && (
+            {status === 'always_allow' && (
               <svg
                 className="w-5 h-5 text-gray-500"
                 xmlns="http://www.w3.org/2000/svg"
@@ -41,7 +72,19 @@ export default function ToolConfirmation({
                 <path strokeLinecap="round" strokeLinejoin="round" d="M5 13l4 4L19 7" />
               </svg>
             )}
-            {status === 'denied' && (
+            {status === 'allow_once' && (
+              <svg
+                className="w-5 h-5 text-gray-500"
+                xmlns="http://www.w3.org/2000/svg"
+                fill="none"
+                viewBox="0 0 24 24"
+                stroke="currentColor"
+                strokeWidth={2}
+              >
+                <path strokeLinecap="round" strokeLinejoin="round" d="M5 13l4 4L19 7" />
+              </svg>
+            )}
+            {status === 'deny' && (
               <svg
                 className="w-5 h-5 text-gray-500"
                 xmlns="http://www.w3.org/2000/svg"
@@ -56,30 +99,48 @@ export default function ToolConfirmation({
             <span className="ml-2 text-textStandard">
               {isClicked
                 ? 'Tool confirmation is not available'
-                : `${snakeToTitleCase(toolName.substring(toolName.lastIndexOf('__') + 2))} is ${status}`}
+                : `${snakeToTitleCase(toolName.substring(toolName.lastIndexOf('__') + 2))} is ${actionDisplay}`}
             </span>
           </div>
+
+          <div className="flex items-center cursor-pointer" onClick={() => setIsModalOpen(true)}>
+            <span className="mr-1 text-textStandard">Change</span>
+            <ChevronRight className="w-4 h-4 ml-1 text-iconStandard" />
+          </div>
         </div>
       ) : (
-        <div className="goose-message-tool bg-bgApp border border-borderSubtle dark:border-gray-700 rounded-b-2xl px-4 pt-4 pb-2 flex gap-4 mt-1">
+        <div className="goose-message-tool bg-bgApp border border-borderSubtle dark:border-gray-700 rounded-b-2xl px-4 pt-2 pb-2 flex gap-2 items-center">
           <button
             className={
               'bg-black text-white dark:bg-white dark:text-black rounded-full px-6 py-2 transition'
             }
-            onClick={() => handleButtonClick(true)}
+            onClick={() => handleButtonClick(ALWAYS_ALLOW)}
           >
-            Allow tool
+            Always Allow
+          </button>
+          <button
+            className={
+              'bg-bgProminent text-white dark:text-white rounded-full px-6 py-2 transition'
+            }
+            onClick={() => handleButtonClick(ALLOW_ONCE)}
+          >
+            Allow Once
           </button>
           <button
             className={
               'bg-white text-black dark:bg-black dark:text-white border border-gray-300 dark:border-gray-700 rounded-full px-6 py-2 transition'
             }
-            onClick={() => handleButtonClick(false)}
+            onClick={() => handleButtonClick(DENY)}
           >
             Deny
           </button>
         </div>
       )}
+
+      {/* Modal for updating tool permission */}
+      {isModalOpen && (
+        <PermissionModal onClose={handleModalClose} extensionName={getExtensionName(toolName)} />
+      )}
     </>
   );
 }
diff --git a/ui/desktop/src/components/settings_v2/permission/PermissionModal.tsx b/ui/desktop/src/components/settings_v2/permission/PermissionModal.tsx
new file mode 100644
index 00000000..889455f7
--- /dev/null
+++ b/ui/desktop/src/components/settings_v2/permission/PermissionModal.tsx
@@ -0,0 +1,192 @@
+import { useEffect, useState } from 'react';
+import { Button } from '../../ui/button';
+import { ChevronDownIcon, SlidersHorizontal } from 'lucide-react';
+import { getTools, PermissionLevel, ToolInfo, upsertPermissions } from '../../../api';
+import * as Dialog from '@radix-ui/react-dialog';
+import * as DropdownMenu from '@radix-ui/react-dropdown-menu';
+
+function getFirstSentence(text: string): string {
+  const match = text.match(/^([^.?!]+[.?!])/);
+  return match ? match[0] : '';
+}
+
+interface PermissionModalProps {
+  extensionName: string;
+  onClose: () => void;
+}
+
+export default function PermissionModal({ extensionName, onClose }: PermissionModalProps) {
+  const permissionOptions = [
+    { value: 'always_allow', label: 'Always allow' },
+    { value: 'ask_before', label: 'Ask before' },
+    { value: 'never_allow', label: 'Never allow' },
+  ] as { value: PermissionLevel; label: string }[];
+
+  const [tools, setTools] = useState<ToolInfo[]>([]);
+  const [updatedPermissions, setUpdatedPermissions] = useState<Record<string, string>>({});
+
+  useEffect(() => {
+    const fetchTools = async () => {
+      try {
+        const response = await getTools({ query: { extension_name: extensionName } });
+        if (response.error) {
+          console.error('Failed to get tools');
+        } else {
+          setTools(response.data || []);
+        }
+      } catch (err) {
+        console.error('Error fetching tools:', err);
+      }
+    };
+
+    fetchTools();
+  }, [extensionName]);
+
+  const handleSettingChange = (toolName: string, newPermission: PermissionLevel) => {
+    setUpdatedPermissions((prev) => ({
+      ...prev,
+      [toolName]: newPermission,
+    }));
+  };
+
+  const handleSave = async () => {
+    try {
+      const payload = {
+        tool_permissions: Object.entries(updatedPermissions).map(([toolName, permission]) => ({
+          tool_name: toolName,
+          permission: permission as PermissionLevel,
+        })),
+      };
+
+      if (payload.tool_permissions.length === 0) {
+        onClose();
+        return;
+      }
+
+      const response = await upsertPermissions({
+        body: payload,
+      });
+      if (response.error) {
+        console.error('Failed to save permissions:', response.error);
+      } else {
+        console.log('Permissions updated successfully');
+        onClose();
+      }
+    } catch (err) {
+      console.error('Error saving permissions:', err);
+    }
+  };
+
+  const footerContent = (
+    <>
+      <Button
+        onClick={handleSave}
+        className="w-full h-[60px] rounded-none border-b border-borderSubtle bg-transparent hover:bg-bgSubtle text-textProminent font-medium text-md"
+      >
+        Save Changes
+      </Button>
+      <Button
+        onClick={onClose}
+        variant="ghost"
+        className="w-full h-[60px] rounded-none hover:bg-bgSubtle text-textSubtle hover:text-textStandard text-md font-regular"
+      >
+        Cancel
+      </Button>
+    </>
+  );
+
+  return (
+    <Dialog.Root open={true} onOpenChange={(open) => !open && onClose()}>
+      <Dialog.Portal>
+        <Dialog.Overlay className="fixed inset-0 bg-black/30 dark:bg-white/20 transition-colors animate-[fadein_200ms_ease-in_forwards]" />
+        <Dialog.Content className="fixed top-[50%] left-[50%] translate-x-[-50%] translate-y-[-50%] w-[500px] max-w-[90vw] bg-bgApp rounded-xl shadow-xl max-h-[90vh] flex flex-col">
+          <div className="p-6">
+            <Dialog.Title className="DialogTitle flex justify-start items-center mb-6">
+              <SlidersHorizontal className="text-iconStandard" size={24} />
+              <p className="ml-2 text-2xl font-semibold text-textStandard">{extensionName}</p>
+            </Dialog.Title>
+            <Dialog.Description className="DialogDescription"></Dialog.Description>
+
+            <div className="flex justify-center items-center h-full">
+              {tools.length === 0 ? (
+                <div className="flex items-center justify-center">
+                  {/* Loading spinner */}
+                  <svg
+                    className="animate-spin h-8 w-8 text-grey-50 dark:text-white"
+                    xmlns="http://www.w3.org/2000/svg"
+                    fill="none"
+                    viewBox="0 0 24 24"
+                  >
+                    <circle
+                      className="opacity-25"
+                      cx="12"
+                      cy="12"
+                      r="10"
+                      stroke="currentColor"
+                      strokeWidth="4"
+                    ></circle>
+                    <path
+                      className="opacity-75"
+                      fill="currentColor"
+                      d="M4 12a8 8 0 018-8v8H4z"
+                    ></path>
+                  </svg>
+                </div>
+              ) : (
+                <div>
+                  {tools.map((tool) => (
+                    <div
+                      key={tool.name}
+                      className="mb-4 flex items-center justify-between grid grid-cols-12"
+                    >
+                      <div className="flex flex-col col-span-8">
+                        <label className="block text-sm font-medium text-textStandard">
+                          {tool.name}
+                        </label>
+                        <p className="text-sm text-gray-500 mb-2">
+                          {getFirstSentence(tool.description)}
+                        </p>
+                      </div>
+                      <DropdownMenu.Root>
+                        <DropdownMenu.Trigger className="flex col-span-4 items-center justify-center bg-bgSubtle text-textStandard rounded-full px-3 py-2">
+                          <span>
+                            {permissionOptions.find(
+                              (option) =>
+                                option.value === (updatedPermissions[tool.name] || tool.permission)
+                            )?.label || 'Ask Before'}
+                          </span>
+                          <ChevronDownIcon className="ml-2 h-4 w-4" />
+                        </DropdownMenu.Trigger>
+                        <DropdownMenu.Portal>
+                          <DropdownMenu.Content className="bg-white dark:bg-bgProminent rounded-lg shadow-md">
+                            {permissionOptions.map((option) => (
+                              <DropdownMenu.Item
+                                key={option.value}
+                                className="px-8 py-2 rounded-lg hover:cursor-pointer hover:bg-bgSubtle text-textStandard"
+                                onSelect={() =>
+                                  handleSettingChange(tool.name, option.value as PermissionLevel)
+                                }
+                              >
+                                {option.label}
+                              </DropdownMenu.Item>
+                            ))}
+                          </DropdownMenu.Content>
+                        </DropdownMenu.Portal>
+                      </DropdownMenu.Root>
+                    </div>
+                  ))}
+                </div>
+              )}
+            </div>
+          </div>
+
+          {footerContent && (
+            <div className="border-t border-borderSubtle bg-bgApp w-full rounded-b-xl overflow-hidden">
+              {footerContent}
+            </div>
+          )}
+        </Dialog.Content>
+      </Dialog.Portal>
+    </Dialog.Root>
+  );
+}
diff --git a/ui/desktop/src/utils/toolConfirm.ts b/ui/desktop/src/utils/toolConfirm.ts
index 19c8bfd9..3b0f3f55 100644
--- a/ui/desktop/src/utils/toolConfirm.ts
+++ b/ui/desktop/src/utils/toolConfirm.ts
@@ -1,6 +1,6 @@
 import { getApiUrl, getSecretKey } from '../config';
 
-export async function ConfirmToolRequest(requesyId: string, confirmed: boolean) {
+export async function ConfirmToolRequest(requesyId: string, action: string) {
   try {
     const response = await fetch(getApiUrl('/confirm'), {
       method: 'POST',
@@ -10,7 +10,7 @@ export async function ConfirmToolRequest(requesyId: string, confirmed: boolean)
       },
       body: JSON.stringify({
         id: requesyId,
-        confirmed,
+        action,
       }),
     });