diff --git a/packages/coding-agent/CHANGELOG.md b/packages/coding-agent/CHANGELOG.md
index 4eeb7988..d6ab7f14 100644
--- a/packages/coding-agent/CHANGELOG.md
+++ b/packages/coding-agent/CHANGELOG.md
@@ -4,6 +4,7 @@
 
 ### Fixed
 
+- Fixed `sessionDir` in `settings.json` to expand `~`, so portable session-directory settings no longer require a shell wrapper ([#3514](https://github.com/badlogic/pi-mono/issues/3514))
 - Fixed parallel tool-call rows to leave the pending state as soon as each tool is finalized, while still appending persisted tool results in assistant source order ([#3503](https://github.com/badlogic/pi-mono/issues/3503))
 - Fixed exported session markdown to render Markdown while showing HTML-like message content such as `<file name="...">...</file>` verbatim, so shared sessions match the TUI instead of letting the browser interpret message text ([#3484](https://github.com/badlogic/pi-mono/issues/3484))
 
diff --git a/packages/coding-agent/docs/settings.md b/packages/coding-agent/docs/settings.md
index 63d4aa88..563c3aa3 100644
--- a/packages/coding-agent/docs/settings.md
+++ b/packages/coding-agent/docs/settings.md
@@ -132,7 +132,7 @@ When a provider requests a retry delay longer than `maxDelayMs` (e.g., Google's
 
 | Setting | Type | Default | Description |
 |---------|------|---------|-------------|
-| `sessionDir` | string | - | Directory where session files are stored. Accepts absolute or relative paths. |
+| `sessionDir` | string | - | Directory where session files are stored. Accepts absolute or relative paths, plus `~`. |
 
 ```json
 { "sessionDir": ".pi/sessions" }
diff --git a/packages/coding-agent/src/core/settings-manager.ts b/packages/coding-agent/src/core/settings-manager.ts
index 8700029a..fb923770 100644
--- a/packages/coding-agent/src/core/settings-manager.ts
+++ b/packages/coding-agent/src/core/settings-manager.ts
@@ -1,5 +1,6 @@
 import type { Transport } from "@mariozechner/pi-ai";
 import { existsSync, mkdirSync, readFileSync, writeFileSync } from "fs";
+import { homedir } from "os";
 import { dirname, join } from "path";
 import lockfile from "proper-lockfile";
 import { CONFIG_DIR_NAME, getAgentDir } from "../config.js";
@@ -534,7 +535,17 @@ export class SettingsManager {
 	}
 
 	getSessionDir(): string | undefined {
-		return this.settings.sessionDir;
+		const sessionDir = this.settings.sessionDir;
+		if (!sessionDir) {
+			return sessionDir;
+		}
+		if (sessionDir === "~") {
+			return homedir();
+		}
+		if (sessionDir.startsWith("~/")) {
+			return join(homedir(), sessionDir.slice(2));
+		}
+		return sessionDir;
 	}
 
 	getDefaultProvider(): string | undefined {
diff --git a/packages/coding-agent/test/settings-manager.test.ts b/packages/coding-agent/test/settings-manager.test.ts
index 2461b601..d01b1363 100644
--- a/packages/coding-agent/test/settings-manager.test.ts
+++ b/packages/coding-agent/test/settings-manager.test.ts
@@ -1,4 +1,5 @@
 import { existsSync, mkdirSync, readFileSync, rmSync, writeFileSync } from "fs";
+import { homedir } from "os";
 import { join } from "path";
 import { afterEach, beforeEach, describe, expect, it } from "vitest";
 import { SettingsManager } from "../src/core/settings-manager.js";
@@ -308,5 +309,11 @@ describe("SettingsManager", () => {
 			const manager = SettingsManager.create(projectDir, agentDir);
 			expect(manager.getSessionDir()).toBe("./sessions");
 		});
+
+		it("should expand ~ in sessionDir", () => {
+			writeFileSync(join(agentDir, "settings.json"), JSON.stringify({ sessionDir: "~/sessions" }));
+			const manager = SettingsManager.create(projectDir, agentDir);
+			expect(manager.getSessionDir()).toBe(join(homedir(), "sessions"));
+		});
 	});
 });