diff --git a/frontend/src/api/client.ts b/frontend/src/api/client.ts
index f11c1d6..bcaa5cf 100644
--- a/frontend/src/api/client.ts
+++ b/frontend/src/api/client.ts
@@ -11,6 +11,7 @@ export type WsRequest =
 			type: "permission_response";
 			request_id: string;
 			approved: boolean;
+			always_allow: boolean;
 	  }
 	| { type: "ping" };
 
@@ -469,8 +470,17 @@ export class ChatWebSocket {
 		this.send({ type: "cancel" });
 	}
 
-	sendPermissionResponse(requestId: string, approved: boolean) {
-		this.send({ type: "permission_response", request_id: requestId, approved });
+	sendPermissionResponse(
+		requestId: string,
+		approved: boolean,
+		alwaysAllow = false,
+	) {
+		this.send({
+			type: "permission_response",
+			request_id: requestId,
+			approved,
+			always_allow: alwaysAllow,
+		});
 	}
 
 	close() {
diff --git a/frontend/src/components/Chat.tsx b/frontend/src/components/Chat.tsx
index 962fe55..dfe39e9 100644
--- a/frontend/src/components/Chat.tsx
+++ b/frontend/src/components/Chat.tsx
@@ -578,10 +578,14 @@ export function Chat({ projectPath, onCloseProject }: ChatProps) {
 		}
 	};
 
-	const handlePermissionResponse = (approved: boolean) => {
+	const handlePermissionResponse = (approved: boolean, alwaysAllow = false) => {
 		const current = permissionQueue[0];
 		if (!current) return;
-		wsRef.current?.sendPermissionResponse(current.requestId, approved);
+		wsRef.current?.sendPermissionResponse(
+			current.requestId,
+			approved,
+			alwaysAllow,
+		);
 		setPermissionQueue((prev) => prev.slice(1));
 	};
 
@@ -1095,6 +1099,21 @@ export function Chat({ projectPath, onCloseProject }: ChatProps) {
 							>
 								Approve
 							</button>
+							<button
+								type="button"
+								onClick={() => handlePermissionResponse(true, true)}
+								style={{
+									padding: "10px 20px",
+									borderRadius: "8px",
+									border: "none",
+									backgroundColor: "#4caf50",
+									color: "#fff",
+									cursor: "pointer",
+									fontSize: "0.9em",
+								}}
+							>
+								Always Allow
+							</button>
 						</div>
 					</div>
 				</div>
diff --git a/frontend/src/types.ts b/frontend/src/types.ts
index b5df52c..19a1918 100644
--- a/frontend/src/types.ts
+++ b/frontend/src/types.ts
@@ -53,6 +53,7 @@ export type WsRequest =
 			type: "permission_response";
 			request_id: string;
 			approved: boolean;
+			always_allow: boolean;
 	  };
 
 export type WsResponse =
diff --git a/server/src/http/context.rs b/server/src/http/context.rs
index 9e2726a..370f3ed 100644
--- a/server/src/http/context.rs
+++ b/server/src/http/context.rs
@@ -7,6 +7,18 @@ use poem::http::StatusCode;
 use std::sync::Arc;
 use tokio::sync::{broadcast, mpsc, oneshot};
 
+/// The user's decision when responding to a permission dialog.
+#[derive(Debug, Clone, Copy, PartialEq, Eq)]
+pub enum PermissionDecision {
+    /// One-time denial.
+    Deny,
+    /// One-time approval.
+    Approve,
+    /// Approve and persist the rule to `.claude/settings.json` so Claude Code's
+    /// built-in permission system handles future checks without prompting.
+    AlwaysAllow,
+}
+
 /// A permission request forwarded from the MCP `prompt_permission` tool to the
 /// active WebSocket session. The MCP handler blocks on `response_tx` until the
 /// user approves or denies via the frontend dialog.
@@ -14,7 +26,7 @@ pub struct PermissionForward {
     pub request_id: String,
     pub tool_name: String,
     pub tool_input: serde_json::Value,
-    pub response_tx: oneshot::Sender<bool>,
+    pub response_tx: oneshot::Sender<PermissionDecision>,
 }
 
 #[derive(Clone)]
@@ -82,4 +94,13 @@ mod tests {
         let err = bad_request(String::new());
         assert_eq!(err.status(), StatusCode::BAD_REQUEST);
     }
+
+    #[test]
+    fn permission_decision_equality() {
+        assert_eq!(PermissionDecision::Deny, PermissionDecision::Deny);
+        assert_eq!(PermissionDecision::Approve, PermissionDecision::Approve);
+        assert_eq!(PermissionDecision::AlwaysAllow, PermissionDecision::AlwaysAllow);
+        assert_ne!(PermissionDecision::Deny, PermissionDecision::Approve);
+        assert_ne!(PermissionDecision::Approve, PermissionDecision::AlwaysAllow);
+    }
 }
diff --git a/server/src/http/mcp.rs b/server/src/http/mcp.rs
index c15eca7..1566340 100644
--- a/server/src/http/mcp.rs
+++ b/server/src/http/mcp.rs
@@ -1793,6 +1793,93 @@ fn tool_get_server_logs(args: &Value) -> Result<String, String> {
     Ok(all_lines[start..].join("\n"))
 }
 
+/// Generate a Claude Code permission rule string for the given tool name and input.
+///
+/// - `Edit` / `Write` / `Read` / `Grep` / `Glob` etc. → just the tool name
+/// - `Bash` → `Bash(first_word *)` derived from the `command` field in `tool_input`
+/// - `mcp__*` → the full tool name (e.g. `mcp__story-kit__create_story`)
+fn generate_permission_rule(tool_name: &str, tool_input: &Value) -> String {
+    if tool_name == "Bash" {
+        // Extract command from tool_input.command and use first word as prefix
+        let command_str = tool_input
+            .get("command")
+            .and_then(|v| v.as_str())
+            .unwrap_or("");
+        let first_word = command_str.split_whitespace().next().unwrap_or("unknown");
+        format!("Bash({first_word} *)")
+    } else {
+        // For Edit, Write, Read, Glob, Grep, MCP tools, etc. — use the tool name directly
+        tool_name.to_string()
+    }
+}
+
+/// Add a permission rule to `.claude/settings.json` in the project root.
+/// Does nothing if the rule already exists. Creates the file if missing.
+fn add_permission_rule(project_root: &std::path::Path, rule: &str) -> Result<(), String> {
+    let claude_dir = project_root.join(".claude");
+    fs::create_dir_all(&claude_dir)
+        .map_err(|e| format!("Failed to create .claude/ directory: {e}"))?;
+
+    let settings_path = claude_dir.join("settings.json");
+    let mut settings: Value = if settings_path.exists() {
+        let content = fs::read_to_string(&settings_path)
+            .map_err(|e| format!("Failed to read settings.json: {e}"))?;
+        serde_json::from_str(&content)
+            .map_err(|e| format!("Failed to parse settings.json: {e}"))?
+    } else {
+        json!({ "permissions": { "allow": [] } })
+    };
+
+    let allow_arr = settings
+        .pointer_mut("/permissions/allow")
+        .and_then(|v| v.as_array_mut());
+
+    let allow = match allow_arr {
+        Some(arr) => arr,
+        None => {
+            // Ensure the structure exists
+            settings
+                .as_object_mut()
+                .unwrap()
+                .entry("permissions")
+                .or_insert(json!({ "allow": [] }));
+            settings
+                .pointer_mut("/permissions/allow")
+                .unwrap()
+                .as_array_mut()
+                .unwrap()
+        }
+    };
+
+    // Check for duplicates — exact string match
+    let rule_value = Value::String(rule.to_string());
+    if allow.contains(&rule_value) {
+        return Ok(());
+    }
+
+    // Also check for wildcard coverage: if "mcp__story-kit__*" exists, don't add
+    // a more specific "mcp__story-kit__create_story".
+    let dominated = allow.iter().any(|existing| {
+        if let Some(pat) = existing.as_str()
+            && let Some(prefix) = pat.strip_suffix('*')
+        {
+            return rule.starts_with(prefix);
+        }
+        false
+    });
+    if dominated {
+        return Ok(());
+    }
+
+    allow.push(rule_value);
+
+    let pretty =
+        serde_json::to_string_pretty(&settings).map_err(|e| format!("Failed to serialize: {e}"))?;
+    fs::write(&settings_path, pretty)
+        .map_err(|e| format!("Failed to write settings.json: {e}"))?;
+    Ok(())
+}
+
 /// MCP tool called by Claude Code via `--permission-prompt-tool`.
 ///
 /// Forwards the permission request through the shared channel to the active
@@ -1821,7 +1908,9 @@ async fn tool_prompt_permission(args: &Value, ctx: &AppContext) -> Result<String
         })
         .map_err(|_| "No active WebSocket session to receive permission request".to_string())?;
 
-    let approved = tokio::time::timeout(
+    use crate::http::context::PermissionDecision;
+
+    let decision = tokio::time::timeout(
         std::time::Duration::from_secs(300),
         response_rx,
     )
@@ -1833,7 +1922,19 @@ async fn tool_prompt_permission(args: &Value, ctx: &AppContext) -> Result<String
     })?
     .map_err(|_| "Permission response channel closed unexpectedly".to_string())?;
 
-    if approved {
+    if decision == PermissionDecision::AlwaysAllow {
+        // Persist the rule so Claude Code won't prompt again for this tool.
+        if let Some(root) = ctx.state.project_root.lock().unwrap().clone() {
+            let rule = generate_permission_rule(&tool_name, &tool_input);
+            if let Err(e) = add_permission_rule(&root, &rule) {
+                slog_warn!("[permission] Failed to write always-allow rule: {e}");
+            } else {
+                slog!("[permission] Added always-allow rule: {rule}");
+            }
+        }
+    }
+
+    if decision == PermissionDecision::Approve || decision == PermissionDecision::AlwaysAllow {
         // Claude Code SDK expects:
         //   Allow:  { behavior: "allow", updatedInput: <record> }
         //   Deny:   { behavior: "deny", message: string }
@@ -3382,7 +3483,7 @@ stage = "coder"
         tokio::spawn(async move {
             let mut rx = perm_rx.lock().await;
             if let Some(forward) = rx.recv().await {
-                let _ = forward.response_tx.send(true);
+                let _ = forward.response_tx.send(crate::http::context::PermissionDecision::Approve);
             }
         });
 
@@ -3414,7 +3515,7 @@ stage = "coder"
         tokio::spawn(async move {
             let mut rx = perm_rx.lock().await;
             if let Some(forward) = rx.recv().await {
-                let _ = forward.response_tx.send(false);
+                let _ = forward.response_tx.send(crate::http::context::PermissionDecision::Deny);
             }
         });
 
@@ -3508,4 +3609,134 @@ stage = "coder"
         let pct = read_coverage_percent_from_json(tmp.path());
         assert!(pct.is_none());
     }
+
+    // ── Permission rule generation tests ─────────────────────────
+
+    #[test]
+    fn generate_rule_for_edit_tool() {
+        let rule = generate_permission_rule("Edit", &json!({}));
+        assert_eq!(rule, "Edit");
+    }
+
+    #[test]
+    fn generate_rule_for_write_tool() {
+        let rule = generate_permission_rule("Write", &json!({}));
+        assert_eq!(rule, "Write");
+    }
+
+    #[test]
+    fn generate_rule_for_bash_git() {
+        let rule =
+            generate_permission_rule("Bash", &json!({"command": "git status"}));
+        assert_eq!(rule, "Bash(git *)");
+    }
+
+    #[test]
+    fn generate_rule_for_bash_cargo() {
+        let rule =
+            generate_permission_rule("Bash", &json!({"command": "cargo test --all"}));
+        assert_eq!(rule, "Bash(cargo *)");
+    }
+
+    #[test]
+    fn generate_rule_for_bash_empty_command() {
+        let rule = generate_permission_rule("Bash", &json!({}));
+        assert_eq!(rule, "Bash(unknown *)");
+    }
+
+    #[test]
+    fn generate_rule_for_mcp_tool() {
+        let rule = generate_permission_rule(
+            "mcp__story-kit__create_story",
+            &json!({"name": "foo"}),
+        );
+        assert_eq!(rule, "mcp__story-kit__create_story");
+    }
+
+    // ── Settings.json writing tests ──────────────────────────────
+
+    #[test]
+    fn add_rule_creates_settings_file_when_missing() {
+        let tmp = tempfile::tempdir().unwrap();
+        add_permission_rule(tmp.path(), "Edit").unwrap();
+
+        let content = fs::read_to_string(tmp.path().join(".claude/settings.json")).unwrap();
+        let settings: Value = serde_json::from_str(&content).unwrap();
+        let allow = settings["permissions"]["allow"].as_array().unwrap();
+        assert!(allow.contains(&json!("Edit")));
+    }
+
+    #[test]
+    fn add_rule_does_not_duplicate_existing() {
+        let tmp = tempfile::tempdir().unwrap();
+        add_permission_rule(tmp.path(), "Edit").unwrap();
+        add_permission_rule(tmp.path(), "Edit").unwrap();
+
+        let content = fs::read_to_string(tmp.path().join(".claude/settings.json")).unwrap();
+        let settings: Value = serde_json::from_str(&content).unwrap();
+        let allow = settings["permissions"]["allow"].as_array().unwrap();
+        let count = allow.iter().filter(|v| v == &&json!("Edit")).count();
+        assert_eq!(count, 1);
+    }
+
+    #[test]
+    fn add_rule_skips_when_wildcard_already_covers() {
+        let tmp = tempfile::tempdir().unwrap();
+        let claude_dir = tmp.path().join(".claude");
+        fs::create_dir_all(&claude_dir).unwrap();
+        fs::write(
+            claude_dir.join("settings.json"),
+            r#"{"permissions":{"allow":["mcp__story-kit__*"]}}"#,
+        )
+        .unwrap();
+
+        add_permission_rule(tmp.path(), "mcp__story-kit__create_story").unwrap();
+
+        let content = fs::read_to_string(claude_dir.join("settings.json")).unwrap();
+        let settings: Value = serde_json::from_str(&content).unwrap();
+        let allow = settings["permissions"]["allow"].as_array().unwrap();
+        assert_eq!(allow.len(), 1);
+        assert_eq!(allow[0], "mcp__story-kit__*");
+    }
+
+    #[test]
+    fn add_rule_appends_to_existing_rules() {
+        let tmp = tempfile::tempdir().unwrap();
+        let claude_dir = tmp.path().join(".claude");
+        fs::create_dir_all(&claude_dir).unwrap();
+        fs::write(
+            claude_dir.join("settings.json"),
+            r#"{"permissions":{"allow":["Edit"]}}"#,
+        )
+        .unwrap();
+
+        add_permission_rule(tmp.path(), "Write").unwrap();
+
+        let content = fs::read_to_string(claude_dir.join("settings.json")).unwrap();
+        let settings: Value = serde_json::from_str(&content).unwrap();
+        let allow = settings["permissions"]["allow"].as_array().unwrap();
+        assert_eq!(allow.len(), 2);
+        assert!(allow.contains(&json!("Edit")));
+        assert!(allow.contains(&json!("Write")));
+    }
+
+    #[test]
+    fn add_rule_preserves_other_settings_fields() {
+        let tmp = tempfile::tempdir().unwrap();
+        let claude_dir = tmp.path().join(".claude");
+        fs::create_dir_all(&claude_dir).unwrap();
+        fs::write(
+            claude_dir.join("settings.json"),
+            r#"{"permissions":{"allow":["Edit"]},"enabledMcpjsonServers":["story-kit"]}"#,
+        )
+        .unwrap();
+
+        add_permission_rule(tmp.path(), "Write").unwrap();
+
+        let content = fs::read_to_string(claude_dir.join("settings.json")).unwrap();
+        let settings: Value = serde_json::from_str(&content).unwrap();
+        let servers = settings["enabledMcpjsonServers"].as_array().unwrap();
+        assert_eq!(servers.len(), 1);
+        assert_eq!(servers[0], "story-kit");
+    }
 }
diff --git a/server/src/http/ws.rs b/server/src/http/ws.rs
index 755fb09..07f212d 100644
--- a/server/src/http/ws.rs
+++ b/server/src/http/ws.rs
@@ -1,4 +1,4 @@
-use crate::http::context::AppContext;
+use crate::http::context::{AppContext, PermissionDecision};
 use crate::http::workflow::{PipelineState, load_pipeline_state};
 use crate::io::onboarding;
 use crate::io::watcher::WatcherEvent;
@@ -29,6 +29,8 @@ enum WsRequest {
     PermissionResponse {
         request_id: String,
         approved: bool,
+        #[serde(default)]
+        always_allow: bool,
     },
     /// Heartbeat ping from the client. The server responds with `Pong` so the
     /// client can detect stale (half-closed) connections.
@@ -250,7 +252,7 @@ pub async fn ws_handler(ws: WebSocket, ctx: Data<&Arc<AppContext>>) -> impl poem
         // Permission requests arrive from the MCP `prompt_permission` tool via
         // `ctx.perm_rx` and are forwarded to the client as `PermissionRequest`.
         // When the client responds, we resolve the corresponding oneshot.
-        let mut pending_perms: HashMap<String, oneshot::Sender<bool>> = HashMap::new();
+        let mut pending_perms: HashMap<String, oneshot::Sender<PermissionDecision>> = HashMap::new();
 
         loop {
             // Outer loop: wait for the next WebSocket message.
@@ -324,9 +326,16 @@ pub async fn ws_handler(ws: WebSocket, ctx: Data<&Arc<AppContext>>) -> impl poem
                             // (permission responses and cancellations).
                             Some(Ok(WsMessage::Text(inner_text))) = stream.next() => {
                                 match serde_json::from_str::<WsRequest>(&inner_text) {
-                                    Ok(WsRequest::PermissionResponse { request_id, approved }) => {
+                                    Ok(WsRequest::PermissionResponse { request_id, approved, always_allow }) => {
                                         if let Some(resp_tx) = pending_perms.remove(&request_id) {
-                                            let _ = resp_tx.send(approved);
+                                            let decision = if always_allow {
+                                                PermissionDecision::AlwaysAllow
+                                            } else if approved {
+                                                PermissionDecision::Approve
+                                            } else {
+                                                PermissionDecision::Deny
+                                            };
+                                            let _ = resp_tx.send(decision);
                                         }
                                     }
                                     Ok(WsRequest::Cancel) => {
@@ -457,9 +466,11 @@ mod tests {
             WsRequest::PermissionResponse {
                 request_id,
                 approved,
+                always_allow,
             } => {
                 assert_eq!(request_id, "req-42");
                 assert!(approved);
+                assert!(!always_allow);
             }
             _ => panic!("expected PermissionResponse variant"),
         }
@@ -477,9 +488,34 @@ mod tests {
             WsRequest::PermissionResponse {
                 request_id,
                 approved,
+                always_allow,
             } => {
                 assert_eq!(request_id, "req-99");
                 assert!(!approved);
+                assert!(!always_allow);
+            }
+            _ => panic!("expected PermissionResponse variant"),
+        }
+    }
+
+    #[test]
+    fn deserialize_permission_response_always_allow() {
+        let json = r#"{
+            "type": "permission_response",
+            "request_id": "req-100",
+            "approved": true,
+            "always_allow": true
+        }"#;
+        let req: WsRequest = serde_json::from_str(json).unwrap();
+        match req {
+            WsRequest::PermissionResponse {
+                request_id,
+                approved,
+                always_allow,
+            } => {
+                assert_eq!(request_id, "req-100");
+                assert!(approved);
+                assert!(always_allow);
             }
             _ => panic!("expected PermissionResponse variant"),
         }