fix: closing a transaction or signature approval window leaves the request pending (closes #673)

Closing a transaction or signature approval window no longer rejects the request; only Cancel does. The browser can close that window when the user clicks away, for example to copy the password from a password manager. The request stays pending and the site gets no answer. Pressing the toolbar button opens the oldest such request, unless an approved attempt still holds it. A Reject the background refuses keeps the window open with the background's message. The worker points the toolbar back at the wallet when it starts.

While such a request waits, the transaction slot stays held, so another site's eth_sendTransaction gets -32002. An address switch still rejects pending approvals with 4001.

Model: opus-5-5

tests/approvalWindow.test.js

@@ -12,6 +12,7 @@ const {
     cleanupPopup,
     settle,
     unversionedValidProfile,
+    ADDRESS,
 } = require("./support/popupBoot");
 
 afterEach(cleanupPopup);
@@ -174,3 +175,136 @@ test("a connection prompt in the toolbar popup leaves the browser window alone",
     expect(windows.updates).toEqual([]);
     expect(env.pageErrors).toEqual([]);
 });
+
+// Each row holds a transaction or signature approval as the background
+// describes it, plus the element ids of the screen that shows it. `refusal` is
+// the message the background refuses a Reject with.
+const TX_AND_SIGN_APPROVALS = [
+    {
+        kind: "transaction",
+        view: "approve-tx",
+        reject: "btn-reject-tx",
+        error: "approve-tx-error",
+        type: "AUTISTMASK_TX_RESPONSE",
+        refusal: "This transaction is already being sent.",
+        approval: {
+            type: "tx",
+            approvedFrom: ADDRESS,
+            approvedTx: {
+                chainId: 1,
+                to: ADDRESS,
+                value: "0",
+                data: "0x",
+                gasLimit: "21000",
+                maxFeePerGas: "1000000000",
+                maxPriorityFeePerGas: "1000000000",
+                nonce: 0,
+            },
+        },
+    },
+    {
+        kind: "signature",
+        view: "approve-sign",
+        reject: "btn-reject-sign",
+        error: "approve-sign-error",
+        type: "AUTISTMASK_SIGN_RESPONSE",
+        refusal: "This request is already being signed.",
+        approval: {
+            type: "sign",
+            approvedFrom: ADDRESS,
+            signParams: {
+                method: "personal_sign",
+                message: "0x48656c6c6f",
+                from: ADDRESS,
+            },
+        },
+    },
+];
+
+// A closed transaction or signature window leaves its request pending
+// (https://git.eeqj.de/sneak/AutistMask/issues/673). So Reject closes the
+// window only once the background has the rejection. A message sent as the
+// window closes can be lost, and the request would stay pending although the
+// user rejected it.
+test.each(TX_AND_SIGN_APPROVALS)(
+    "Reject on a $kind approval closes the window only once the background has answered",
+    async ({ view, reject, type, approval }) => {
+        let describeApproval = null;
+        let answerReject = null;
+        const sent = [];
+        const env = await bootPopup(unversionedValidProfile(), {
+            search: "?approval=approval-1",
+            runtime: {
+                connect: () => ({ postMessage: () => {} }),
+                sendMessage: (msg, reply) => {
+                    if (msg.type === "AUTISTMASK_GET_APPROVAL") {
+                        describeApproval = reply;
+                    }
+                    if (msg.type === type) {
+                        sent.push(msg);
+                        answerReject = reply;
+                    }
+                },
+            },
+        });
+        describeApproval({
+            ...approval,
+            origin: "https://dapp.example",
+            isPhishingDomain: false,
+        });
+        await settle();
+        expect(env.visibleViews()).toEqual([view]);
+        const close = jest.fn();
+        globalThis.window.close = close;
+
+        const clicked = env.click(reject);
+        await settle();
+        expect(sent).toEqual([{ type, id: "approval-1", approved: false }]);
+        expect(close).not.toHaveBeenCalled();
+
+        answerReject(null);
+        await clicked;
+        expect(close).toHaveBeenCalledTimes(1);
+        expect(env.pageErrors).toEqual([]);
+    },
+);
+
+// After Confirm or Sign, the background refuses a Reject while the transaction
+// is being sent or the signature checked. The request is not rejected then, so
+// the window stays open and shows the background's message.
+test.each(TX_AND_SIGN_APPROVALS)(
+    "Reject on a $kind approval that the background refuses shows the background's message and keeps the window open",
+    async ({ view, reject, error, type, refusal, approval }) => {
+        let describeApproval = null;
+        let answerReject = null;
+        const env = await bootPopup(unversionedValidProfile(), {
+            search: "?approval=approval-1",
+            runtime: {
+                connect: () => ({ postMessage: () => {} }),
+                sendMessage: (msg, reply) => {
+                    if (msg.type === "AUTISTMASK_GET_APPROVAL") {
+                        describeApproval = reply;
+                    }
+                    if (msg.type === type) answerReject = reply;
+                },
+            },
+        });
+        describeApproval({
+            ...approval,
+            origin: "https://dapp.example",
+            isPhishingDomain: false,
+        });
+        await settle();
+        const close = jest.fn();
+        globalThis.window.close = close;
+
+        const clicked = env.click(reject);
+        await settle();
+        answerReject({ error: refusal, retryable: false });
+        await clicked;
+        expect(close).not.toHaveBeenCalled();
+        expect(env.visibleViews()).toEqual([view]);
+        expect(env.text(error)).toBe(refusal);
+        expect(env.pageErrors).toEqual([]);
+    },
+);

tests/backgroundApproval.test.js

@@ -241,10 +241,11 @@ function loadBackground(options) {
     let connectListener = null;
     const created = [];
     const removed = [];
-    // Every URL the background put on the browser action. A site approval
-    // raised through action.openPopup() opens no window at all, so this is
-    // the only place its id appears.
-    const actionPopups = [];
+    // Every URL the background put on the browser action. When a test gives
+    // the URL the action holds before the worker starts, that URL comes
+    // first. A site approval raised through action.openPopup() opens no
+    // window at all, so this is the only place its id appears.
+    const actionPopups = opts.toolbarPopup ? [opts.toolbarPopup] : [];
     const openPopup = jest.fn(() => Promise.resolve());
 
     global.chrome = {
@@ -774,10 +775,9 @@ describe("one transaction approval at a time", () => {
 
     // The user closes an approval window that looks hung while the attempt
     // behind it is still running, and that attempt then fails in a way that
-    // would normally leave the approval standing for a retry. There is no
-    // window left to retry in, so leaving it standing answers the requesting
-    // page never — and holds the slot for the life of the worker with it.
-    test("an approval whose window closed under a failed attempt is answered, and frees the next request", async () => {
+    // leaves the approval standing for a retry. The toolbar popup opens it, so
+    // the user can still retry it, and answering it frees the slot.
+    test("an approval whose window closed under a failed attempt is retried from the toolbar popup, and frees the next request", async () => {
         const stalled = deferred();
         const bg = loadBackground();
 
@@ -808,11 +808,28 @@ describe("one transaction approval at a time", () => {
 
         stalled.resolve();
         await settle();
-        expect(first.result()).toEqual({
-            error: { code: 4001, message: "User rejected the request." },
-        });
+        expect(first.result()).toBeNull();
+        expect(bg.actionPopups[bg.actionPopups.length - 1]).toBe(
+            "src/popup/index.html?approval=" + first.id(),
+        );
 
         bg.setStateReadHook(null);
+        bg.broadcastTransaction.mockResolvedValue({ hash: "0xfeed" });
+        bg.send(
+            {
+                type: "AUTISTMASK_TX_RESPONSE",
+                id: first.id(),
+                approved: true,
+                rawSignedTx: await signedAtNonce(NONCE),
+            },
+            { url: bg.fromPopup.url },
+        );
+        await settle();
+        expect(first.result()).toEqual({ result: "0xfeed" });
+        expect(bg.actionPopups[bg.actionPopups.length - 1]).toBe(
+            "src/popup/index.html",
+        );
+
         const second = bg.requestTx();
         await settle();
         expect(second.result()).toBeNull();
@@ -853,8 +870,10 @@ describe("one transaction approval at a time", () => {
         const first = bg.requestTx();
         await settle();
 
-        // The user closes the approval window, which rejects it.
-        bg.closeWindow(1);
+        bg.send(
+            { type: "AUTISTMASK_TX_RESPONSE", id: first.id(), approved: false },
+            { url: bg.fromPopup.url },
+        );
         await settle();
         expect(first.result()).toEqual({
             error: { code: 4001, message: "User rejected the request." },
@@ -897,7 +916,7 @@ describe("the worker keeps running while an approval is pending", () => {
         try {
             const bg = loadBackground();
             const calls = global.chrome.runtime.getPlatformInfo;
-            bg.requestTx();
+            const pending = bg.requestTx();
             await settle();
             expect(startTimer).toHaveBeenCalledTimes(1);
             expect(startTimer.mock.calls[0][1]).toBe(20000);
@@ -906,11 +925,23 @@ describe("the worker keeps running while an approval is pending", () => {
             tick();
             expect(calls).toHaveBeenCalledTimes(1);
 
-            // The user closes the approval window, which rejects it.
+            // A closed window leaves the approval pending, so the calls go on.
             bg.closeWindow(1);
             await settle();
             tick();
-            expect(calls).toHaveBeenCalledTimes(1);
+            expect(calls).toHaveBeenCalledTimes(2);
+
+            bg.send(
+                {
+                    type: "AUTISTMASK_TX_RESPONSE",
+                    id: pending.id(),
+                    approved: false,
+                },
+                { url: bg.fromPopup.url },
+            );
+            await settle();
+            tick();
+            expect(calls).toHaveBeenCalledTimes(2);
             expect(stopTimer).toHaveBeenCalledWith(1);
         } finally {
             startTimer.mockRestore();
@@ -1841,6 +1872,237 @@ describe("the interlock releases a failed attempt", () => {
     });
 });
 
+// A transaction or signature approval stays pending when its window closes.
+// The browser can close that window when the user clicks away from it, for
+// example to copy the password from a password manager. The toolbar popup then
+// opens the approval, and the user answers it there
+// (https://git.eeqj.de/sneak/AutistMask/issues/673).
+describe("a closed approval window leaves the request pending", () => {
+    // The URL the toolbar popup opens now.
+    function toolbarPopup(bg) {
+        return bg.actionPopups[bg.actionPopups.length - 1];
+    }
+
+    // The timer that keeps the worker running while an approval is pending is
+    // stubbed, so no test here leaves that timer running when it ends.
+    let keepRunningTimer;
+    beforeEach(() => {
+        keepRunningTimer = jest
+            .spyOn(global, "setInterval")
+            .mockImplementation(() => 1);
+    });
+    afterEach(() => {
+        keepRunningTimer.mockRestore();
+    });
+
+    test("the toolbar popup opens a closed transaction approval, and approving it there sends", async () => {
+        const bg = loadBackground();
+        const pending = bg.requestTx();
+        await settle();
+
+        bg.closeWindow(1);
+        await settle();
+        expect(pending.result()).toBeNull();
+        expect(toolbarPopup(bg)).toBe(
+            "src/popup/index.html?approval=" + pending.id(),
+        );
+
+        bg.broadcastTransaction.mockResolvedValue({ hash: "0xfeed" });
+        bg.send(
+            {
+                type: "AUTISTMASK_TX_RESPONSE",
+                id: pending.id(),
+                approved: true,
+                rawSignedTx: await signedAtNonce(NONCE),
+            },
+            { url: bg.fromPopup.url },
+        );
+        await settle();
+        expect(pending.result()).toEqual({ result: "0xfeed" });
+        expect(toolbarPopup(bg)).toBe("src/popup/index.html");
+    });
+
+    test("Reject in the toolbar popup answers 4001, and the toolbar popup opens the wallet again", async () => {
+        const bg = loadBackground();
+        const pending = bg.requestSign();
+        await settle();
+
+        bg.closeWindow(1);
+        await settle();
+        expect(pending.result()).toBeNull();
+        expect(toolbarPopup(bg)).toBe(
+            "src/popup/index.html?approval=" + pending.id(),
+        );
+
+        const reject = bg.send(
+            {
+                type: "AUTISTMASK_SIGN_RESPONSE",
+                id: pending.id(),
+                approved: false,
+            },
+            { url: bg.fromPopup.url },
+        );
+        await settle();
+        expect(pending.result()).toEqual({
+            error: { code: 4001, message: "User rejected the request." },
+        });
+        // The popup closes its window only once this answer arrives.
+        expect(reject.sendResponse).toHaveBeenCalledWith(null);
+        expect(toolbarPopup(bg)).toBe("src/popup/index.html");
+    });
+
+    test("with two closed, the toolbar popup opens the older one first, then the other", async () => {
+        const bg = loadBackground();
+        const sign = bg.requestSign();
+        await settle();
+        const signId = sign.id();
+        const tx = bg.requestTx();
+        await settle();
+
+        // The signature request is in window 1 and the transaction in window
+        // 2. The newer window is closed first.
+        bg.closeWindow(2);
+        bg.closeWindow(1);
+        await settle();
+        expect(toolbarPopup(bg)).toBe(
+            "src/popup/index.html?approval=" + signId,
+        );
+
+        bg.send(
+            { type: "AUTISTMASK_SIGN_RESPONSE", id: signId, approved: false },
+            { url: bg.fromPopup.url },
+        );
+        await settle();
+        expect(toolbarPopup(bg)).toBe(
+            "src/popup/index.html?approval=" + tx.id(),
+        );
+
+        const reject = bg.send(
+            { type: "AUTISTMASK_TX_RESPONSE", id: tx.id(), approved: false },
+            { url: bg.fromPopup.url },
+        );
+        await settle();
+        expect(tx.result()).toEqual({
+            error: { code: 4001, message: "User rejected the request." },
+        });
+        expect(reject.sendResponse).toHaveBeenCalledWith(null);
+        expect(toolbarPopup(bg)).toBe("src/popup/index.html");
+    });
+
+    // The user can close the window while the attempt after Confirm runs. That
+    // attempt answers the request, so meanwhile the toolbar popup opens the
+    // wallet. Opened from the toolbar, the approval would look unanswered.
+    test("when the window closes during an attempt that sends, the toolbar popup keeps opening the wallet", async () => {
+        const bg = loadBackground();
+        const pending = bg.requestTx();
+        await settle();
+
+        const inFlight = deferred();
+        bg.broadcastTransaction.mockReturnValue(inFlight.promise);
+        bg.send(
+            {
+                type: "AUTISTMASK_TX_RESPONSE",
+                id: pending.id(),
+                approved: true,
+                rawSignedTx: await signedAtNonce(NONCE),
+            },
+            { url: bg.fromPopup.url },
+        );
+        await settle();
+        bg.closeWindow(1);
+        await settle();
+        expect(toolbarPopup(bg)).toBe("src/popup/index.html");
+
+        inFlight.resolve({ hash: "0xfeed" });
+        await settle();
+        expect(pending.result()).toEqual({ result: "0xfeed" });
+        expect(toolbarPopup(bg)).toBe("src/popup/index.html");
+    });
+
+    test("when the window closes during an attempt that fails retryably, the toolbar popup opens the wallet until the attempt ends, then the approval", async () => {
+        const stalled = deferred();
+        const bg = loadBackground();
+        const pending = bg.requestTx();
+        await settle();
+
+        bg.setStateReadHook(async () => {
+            await stalled.promise;
+            throw new Error("The wallet data could not be read.");
+        });
+        bg.send(
+            {
+                type: "AUTISTMASK_TX_RESPONSE",
+                id: pending.id(),
+                approved: true,
+                rawSignedTx: await signedAtNonce(NONCE),
+            },
+            { url: bg.fromPopup.url },
+        );
+        await settle();
+        bg.closeWindow(1);
+        await settle();
+        expect(toolbarPopup(bg)).toBe("src/popup/index.html");
+
+        stalled.resolve();
+        await settle();
+        expect(pending.result()).toBeNull();
+        expect(toolbarPopup(bg)).toBe(
+            "src/popup/index.html?approval=" + pending.id(),
+        );
+
+        // A retry from the toolbar popup holds the approval again, so the
+        // toolbar popup opens the wallet while that retry runs.
+        bg.setStateReadHook(null);
+        const inFlight = deferred();
+        bg.broadcastTransaction.mockReturnValue(inFlight.promise);
+        bg.send(
+            {
+                type: "AUTISTMASK_TX_RESPONSE",
+                id: pending.id(),
+                approved: true,
+                rawSignedTx: await signedAtNonce(NONCE),
+            },
+            { url: bg.fromPopup.url },
+        );
+        await settle();
+        expect(toolbarPopup(bg)).toBe("src/popup/index.html");
+
+        inFlight.resolve({ hash: "0xfeed" });
+        await settle();
+        expect(pending.result()).toEqual({ result: "0xfeed" });
+        expect(toolbarPopup(bg)).toBe("src/popup/index.html");
+    });
+
+    test("an address switch still rejects a closed approval", async () => {
+        const bg = loadBackground();
+        const pending = bg.requestTx();
+        await settle();
+        bg.closeWindow(1);
+        await settle();
+        expect(pending.result()).toBeNull();
+
+        bg.send(
+            { type: "AUTISTMASK_ACTIVE_CHANGED" },
+            { url: bg.fromPopup.url },
+        );
+        await settle();
+        expect(pending.result()).toEqual({
+            error: { code: 4001, message: "User rejected the request." },
+        });
+        expect(toolbarPopup(bg)).toBe("src/popup/index.html");
+    });
+
+    // The worker can stop while an approval waits with its window closed. The
+    // approval is lost with the worker, but the toolbar popup keeps its URL.
+    // The next worker points the toolbar popup back at the wallet.
+    test("a worker that starts points the toolbar popup back at the wallet", () => {
+        const bg = loadBackground({
+            toolbarPopup: "src/popup/index.html?approval=lost-approval",
+        });
+        expect(toolbarPopup(bg)).toBe("src/popup/index.html");
+    });
+});
+
 // The claim is what makes one approval one broadcast, so it has to hold
 // against everything else that retires an approval, not just against a second
 // AUTISTMASK_TX_RESPONSE. Each of these paths used to resolve the waiting
@@ -1961,20 +2223,6 @@ describe("a claimed approval outlives every other retirement path", () => {
     });
 
     // The refusals above must not cost the rejection its ordinary meaning.
-    test("with no attempt running, closing the window still rejects", async () => {
-        const bg = loadBackground();
-        const pending = bg.requestTx();
-        await settle();
-
-        bg.closeWindow(1);
-        await settle();
-
-        expect(pending.result()).toEqual({
-            error: { code: 4001, message: "User rejected the request." },
-        });
-        expect(bg.broadcastTransaction).not.toHaveBeenCalled();
-    });
-
     test("with no attempt running, an active-address switch still rejects and closes", async () => {
         const bg = loadBackground();
         const pending = bg.requestTx();
@@ -2584,15 +2832,12 @@ describe("a site connection decided as the popup closes", () => {
         });
     });
 
-    // The `isSite &&` half of that skip, which is what keeps it from reaching
-    // a tx or sign approval. The popup connects its port in show() before it
-    // knows the approval's type, and the background sets portConnected without
-    // looking at the type either, so a tx approval in the fallback window
-    // carries the flag too. Without the conjunct the window event would skip
-    // it, windowClosed would never be set, releaseApproval() would never settle
-    // it, and the page would hang — the #271 regression this guard is written
-    // around.
-    test("a tx window closed with the port connected still rejects", async () => {
+    // That skip must not reach a tx or sign approval. The popup connects its
+    // port in show() before it knows the approval's type, and the background
+    // sets portConnected without looking at the type either, so a tx approval
+    // carries the flag too. If the window event skipped it, windowClosed would
+    // never be set, and the toolbar popup would never open the approval.
+    test("a tx window closed with the port connected is still opened by the toolbar popup", async () => {
         const bg = loadBackground();
         const pending = bg.requestTx();
         await settle();
@@ -2600,9 +2845,10 @@ describe("a site connection decided as the popup closes", () => {
         await settle();
         bg.closeWindow(1);
         await settle();
-        expect(pending.result()).toEqual({
-            error: { code: 4001, message: "User rejected the request." },
-        });
+        expect(pending.result()).toBeNull();
+        expect(bg.actionPopups[bg.actionPopups.length - 1]).toBe(
+            "src/popup/index.html?approval=" + pending.id(),
+        );
     });
 });
 
@@ -2994,13 +3240,14 @@ describe("where an approval window opens", () => {
         expect(bg.created[1].left).toBeUndefined();
         expect(bg.created[1].top).toBeUndefined();
 
-        // The request waits on the second window rather than failing:
-        // closing that window is refusing the prompt.
+        // The request waits on the second window rather than failing. Once
+        // that window closes, the toolbar popup opens the request.
         expect(sign.result()).toBeNull();
         bg.closeWindow(2);
         await settle();
-        expect(sign.result()).toEqual({
-            error: { code: 4001, message: "User rejected the request." },
-        });
+        expect(sign.result()).toBeNull();
+        expect(bg.actionPopups[bg.actionPopups.length - 1]).toBe(
+            "src/popup/index.html?approval=" + sign.id(),
+        );
     });
 });

tests/e2e/firefox/run.js

@@ -1035,11 +1035,14 @@ step(
     },
 );
 
+// A closed approval window leaves its request pending, and the toolbar button
+// opens it (https://git.eeqj.de/sneak/AutistMask/issues/673). WebDriver cannot
+// see the toolbar popup, so its page is opened in a tab, at the URL the
+// extension put on the button.
 step(
-    "closing an approval window rejects the request with 4001",
+    "a closed approval window leaves the request pending until it is rejected",
     async (env) => {
         const d = env.driver;
-        const before = env.server.broadcast.length;
 
         await d.switchToWindow(env.dappWindow);
         await startRequest(d, "sign-closed", "personal_sign", [
@@ -1053,15 +1056,45 @@ step(
 
         // Closed, not rejected: this is the windows.onRemoved path, which can
         // only fire if windows.create() handed back a window id for the
-        // approval to be matched against — call site 4 in the issue, and the
-        // reason suppressing that write-back turns this step red.
+        // approval to be matched against. Without that id the toolbar button
+        // never opens the approval, and this step fails.
         await d.closeWindow(env.dappWindow);
-
-        await assertUserRejection(d, "sign-closed", "a closed approval window");
+        const outcome = await settleRequest(d, "sign-closed", 2000);
         assert(
-            env.server.broadcast.length === before,
-            "a closed approval window still put a transaction on the node",
+            outcome.settled === "pending",
+            "closing the approval window answered the page: " +
+                JSON.stringify(outcome),
         );
+
+        await d.switchToWindow(env.popupWindow);
+        const url = await d.executeAsync(
+            `const done = arguments[arguments.length - 1];
+             browser.browserAction.getPopup({}).then(done, (e) => done(String(e)));`,
+        );
+        assert(
+            url.includes("?approval="),
+            "the toolbar button does not open the pending approval: " + url,
+        );
+        const reopened = await d.newWindow("tab");
+        await d.switchToWindow(reopened);
+        await d.navigate(url);
+        await d.waitVisible("#view-approve-sign");
+        await d.click("#btn-reject-sign");
+
+        await d.switchToWindow(env.dappWindow);
+        await assertUserRejection(
+            d,
+            "sign-closed",
+            "the signature request rejected from the toolbar button",
+        );
+
+        // A page may close only a window a script opened, so the tab can
+        // still be open.
+        const left = await d.findWindow((u) => u.includes("?approval="));
+        if (left) {
+            await d.switchToWindow(left);
+            await d.closeWindow(env.dappWindow);
+        }
     },
 );
 

tests/e2e/run.js

@@ -4110,11 +4110,12 @@ async function waitForApprovalWindow(ctx, timeout = 30000) {
 // reservation exists.
 // How long the tab creation above is given to take effect before the request
 // that raises the next prompt is issued. Dismissing a browser-action popup
-// disconnects its port, and src/background/index.js calls resetPopupUrl() on
-// that disconnect; issued too early, the next request's setPopup() is undone
-// by the previous popup's teardown, chrome.action.openPopup() then rejects,
-// and the fallback window it opens dismisses the popup that was just raised —
-// which settles the fresh approval as a rejection before it can be seen.
+// disconnects its port, and src/background/index.js calls
+// updateToolbarPopup() on that disconnect; issued too early, the next
+// request's setPopup() is undone by the previous popup's teardown,
+// chrome.action.openPopup() then rejects, and the fallback window it opens
+// dismisses the popup that was just raised — which settles the fresh approval
+// as a rejection before it can be seen.
 // Every one of those steps was observed. 1.5s is comfortably past it.
 const APPROVAL_TAB_SETTLE_MS = 1500;
 
@@ -4140,6 +4141,17 @@ async function reserveApprovalTab(env) {
     return env.approvalTab;
 }
 
+// The URL the extension has put on the action: the page the toolbar button
+// opens.
+function toolbarPopupUrl(env) {
+    return env.page.evaluate(
+        () =>
+            new Promise((resolve) => {
+                chrome.action.getPopup({}, (u) => resolve(String(u)));
+            }),
+    );
+}
+
 // The site-connection prompt: the window the extension opened if it managed
 // to open one, and the reserved tab at the action's approval URL otherwise.
 async function openSiteApprovalPopup(env, timeout = 30000) {
@@ -4150,12 +4162,7 @@ async function openSiteApprovalPopup(env, timeout = 30000) {
             .find((p) => !p.isClosed() && p.url().includes("?approval="));
         if (existing) return existing;
 
-        const url = await env.page.evaluate(
-            () =>
-                new Promise((resolve) => {
-                    chrome.action.getPopup({}, (u) => resolve(String(u)));
-                }),
-        );
+        const url = await toolbarPopupUrl(env);
         if (url.includes("?approval=")) {
             await env.approvalTab.goto(url);
             return env.approvalTab;
@@ -5027,6 +5034,116 @@ test("eth_sendTransaction rejected broadcasts nothing (#183)", async (env) => {
     );
 });
 
+// A transaction or signature approval stays pending when its window closes.
+// The browser can close that window when the user clicks away from it, for
+// example to copy the password from a password manager. The toolbar button then
+// opens the approval, and the user answers it there
+// (https://git.eeqj.de/sneak/AutistMask/issues/673).
+//
+// This closes the approval window of request `key` and checks that the page
+// has no answer. It then opens the approval again from the toolbar button.
+// Playwright cannot click that button, so its page is opened in a tab, at the
+// URL the extension put on the button.
+async function closeAndReopen(env, key, view) {
+    const approvalWindow = await waitForApprovalWindow(env.ctx);
+    await visible(approvalWindow, view);
+    await approvalWindow.close();
+
+    const outcome = await settleRequest(env.dapp, key, 2000);
+    assert(
+        outcome.settled === "pending",
+        "closing the approval window answered the page: " +
+            JSON.stringify(outcome),
+    );
+
+    const url = await toolbarPopupUrl(env);
+    assert(
+        url.includes("?approval="),
+        "the toolbar button does not open the pending approval: " + url,
+    );
+    const reopened = await env.ctx.newPage();
+    await reopened.goto(url);
+    await visible(reopened, view);
+    return reopened;
+}
+
+// The stub node answers every nonce request with 0, and the wallet refuses a
+// nonce it has already broadcast. A run can therefore approve one dApp
+// transaction only, so here the signature is approved and the transaction
+// rejected.
+test("a closed signature approval is signed from the toolbar button (#673)", async (env) => {
+    await startRequest(env.dapp, "sign-closed", "personal_sign", [
+        SIGN_HEX,
+        env.expectedAddress,
+    ]);
+    const popup = await closeAndReopen(
+        env,
+        "sign-closed",
+        "#view-approve-sign",
+    );
+    let outcome;
+    try {
+        await popup.fill("#approve-sign-password", PASSWORD);
+        await clickAndClose(popup, "#btn-approve-sign");
+        outcome = await settleRequest(env.dapp, "sign-closed");
+    } finally {
+        await closeApprovalPages(env.ctx);
+    }
+    assert(
+        outcome.settled === "resolved",
+        "personal_sign did not resolve: " + JSON.stringify(outcome),
+    );
+    const recovered = getAddress(
+        verifyMessage(getBytes(SIGN_HEX), outcome.result),
+    );
+    assert(
+        recovered === env.expectedAddress,
+        "the personal_sign signature recovers to " +
+            recovered +
+            ", not to the approved address " +
+            env.expectedAddress,
+    );
+
+    const url = await toolbarPopupUrl(env);
+    assert(
+        !url.includes("?approval="),
+        "the toolbar button still opens the answered approval: " + url,
+    );
+});
+
+test("a closed transaction approval is rejected from the toolbar button (#673)", async (env) => {
+    const before = env.routeOpts.broadcastTransactions.length;
+    await startRequest(env.dapp, "tx-closed", "eth_sendTransaction", [
+        {
+            from: env.expectedAddress,
+            to: STUB_COUNTERPARTY,
+            value: toQuantity(TX_VALUE_WEI),
+            data: TX_DATA,
+        },
+    ]);
+    const popup = await closeAndReopen(env, "tx-closed", "#view-approve-tx");
+    try {
+        await clickAndClose(popup, "#btn-reject-tx");
+        await assertUserRejection(
+            env.dapp,
+            "tx-closed",
+            "the transaction rejected from the toolbar button",
+        );
+    } finally {
+        await closeApprovalPages(env.ctx);
+    }
+    assert(
+        env.routeOpts.broadcastTransactions.length === before,
+        "a rejected transaction still reached the RPC",
+    );
+
+    const url = await toolbarPopupUrl(env);
+    assert(
+        !url.includes("?approval="),
+        "the toolbar button still opens the answered approval: " + url,
+    );
+});
+
 // The extension used to centre every approval window on the last focused
 // window. Centred on another approval window, the new one landed where the
 // browser refused to create it, and the request failed with no window at all
@@ -5070,8 +5187,8 @@ test("a prompt raised while another approval window has focus opens its own (#29
     });
     await visible(txWindow, "#view-approve-tx");
 
-    // Closing a window is refusing its prompt, so both answer 4001.
-    await closeApprovalPages(env.ctx);
+    await clickAndClose(txWindow, "#btn-reject-tx");
+    await clickAndClose(signWindow, "#btn-reject-sign");
     await assertUserRejection(env.dapp, "focus-tx", "the transaction prompt");
     await assertUserRejection(env.dapp, "focus-sign", "the sign prompt");
 });
@@ -5678,9 +5795,11 @@ async function main() {
         // for the new one. After a test that passed, its windows get five
         // seconds to close, and one still open then fails the test: it should
         // have closed itself, and closing it here unreported would hide that.
-        // After a test that already failed, they are closed unreported, so
-        // that a prompt it left unanswered does not refuse the next one from
-        // its site.
+        // After a test that already failed, they are closed unreported. That
+        // rejects a site-connection or network-switch prompt it left
+        // unanswered, so the prompt does not refuse the next one from its
+        // site. A transaction or signature approval stays pending, and can
+        // fail the tests after it.
         if (!failure) {
             const deadline = Date.now() + 5000;
             let open;