diff --git a/app/src-tauri/src/aws/permissions.rs b/app/src-tauri/src/aws/permissions.rs
index 6f6c314..cf51d1b 100644
--- a/app/src-tauri/src/aws/permissions.rs
+++ b/app/src-tauri/src/aws/permissions.rs
@@ -135,8 +135,13 @@ impl SdkPermissionApi {
         // hundred simulations) failed a third of its rows with "Rate
         // exceeded" under standard retries (verified live). Adaptive retry
         // backs off client-side once throttled, with room to retry.
+        //
+        // The connection's 30 s operation limit counts the retries' backoff
+        // too, which would cut those ten attempts to about six; the check
+        // gets its own, longer limit, and the UI says it can take a while.
         let iam = aws_sdk_iam::config::Builder::from(cfg)
             .retry_config(aws_config::retry::RetryConfig::adaptive().with_max_attempts(10))
+            .timeout_config(iam_check_timeouts())
             .build();
         SdkPermissionApi {
             iam: aws_sdk_iam::Client::from_conf(iam),
@@ -147,6 +152,17 @@ impl SdkPermissionApi {
     }
 }
 
+/// The whole of one simulation, retries and backoff included. Ten adaptive
+/// attempts with backoff capped at 20 s fit in two minutes.
+pub const IAM_CHECK_OPERATION_TIMEOUT: std::time::Duration = std::time::Duration::from_secs(120);
+
+fn iam_check_timeouts() -> aws_config::timeout::TimeoutConfig {
+    aws_config::timeout::TimeoutConfig::builder()
+        .operation_timeout(IAM_CHECK_OPERATION_TIMEOUT)
+        .operation_attempt_timeout(super::connection::ATTEMPT_TIMEOUT)
+        .build()
+}
+
 impl PermissionApi for SdkPermissionApi {
     async fn resolve_principal(&self, principal: PrincipalArn) -> Result<String, AwsError> {
         identity::resolve_principal(&self.iam, principal).await
diff --git a/app/src-tauri/src/aws/permissions/tests.rs b/app/src-tauri/src/aws/permissions/tests.rs
index 8a883da..ca2217e 100644
--- a/app/src-tauri/src/aws/permissions/tests.rs
+++ b/app/src-tauri/src/aws/permissions/tests.rs
@@ -628,3 +628,13 @@ fn no_probe_is_cloudformation() {
     }
     assert_eq!(Probe::for_action("cloudformation:DescribeStacks"), None);
 }
+
+#[test]
+fn the_iam_check_gets_room_for_its_throttled_retries() {
+    let t = iam_check_timeouts();
+    assert_eq!(t.operation_timeout(), Some(IAM_CHECK_OPERATION_TIMEOUT));
+    assert!(IAM_CHECK_OPERATION_TIMEOUT > crate::aws::connection::OPERATION_TIMEOUT);
+    // Ten adaptive attempts, backoff capped at 20 s, fit inside it.
+    assert!(IAM_CHECK_OPERATION_TIMEOUT >= std::time::Duration::from_secs(9 * 20 / 2 + 20));
+    assert_eq!(t.operation_attempt_timeout(), Some(crate::aws::connection::ATTEMPT_TIMEOUT));
+}
diff --git a/app/src/components/settings/HostsSettings.test.tsx b/app/src/components/settings/HostsSettings.test.tsx
index 7a1c0fa..f6c98e5 100644
--- a/app/src/components/settings/HostsSettings.test.tsx
+++ b/app/src/components/settings/HostsSettings.test.tsx
@@ -1,6 +1,6 @@
 import { describe, it, expect, vi, beforeEach } from "vitest";
 import { fireEvent, render, screen, waitFor, within } from "@testing-library/react";
-import HostsSettings from "./HostsSettings";
+import HostsSettings, { CHECK_IN_PROGRESS } from "./HostsSettings";
 import { useAppState } from "../../store/appState";
 import type { AppSettings, HostConnection, PermissionReport } from "../../lib/types";
 
@@ -140,6 +140,21 @@ describe("HostsSettings", () => {
     expect(screen.getByLabelText("Secret access key")).toHaveValue("");
   });
 
+  it("tells the user a permission check can take a few minutes while it runs", async () => {
+    let finish: (r: PermissionReport) => void = () => {};
+    invoke.mockImplementation(async (cmd: string) => {
+      if (cmd === "list_aws_profiles") return [];
+      if (cmd === "check_aws_permissions") return new Promise<PermissionReport>((res) => (finish = res));
+      throw new Error(`unexpected ${cmd}`);
+    });
+    render(<HostsSettings />);
+    fireEvent.click(screen.getByRole("button", { name: "Check Prod" }));
+    expect(await screen.findByRole("status")).toHaveTextContent(CHECK_IN_PROGRESS);
+    finish(report({}));
+    expect(await screen.findByText("Insufficient")).toBeInTheDocument();
+    expect(screen.queryByText(CHECK_IN_PROGRESS)).not.toBeInTheDocument();
+  });
+
   it("check shows Insufficient with the denied actions and every policy file to copy", async () => {
     const adminFiles = [
       { name: "environment-admin.json", json: '{"Statement":"admin"}' },
diff --git a/app/src/components/settings/HostsSettings.tsx b/app/src/components/settings/HostsSettings.tsx
index 1a6360d..b1653d9 100644
--- a/app/src/components/settings/HostsSettings.tsx
+++ b/app/src/components/settings/HostsSettings.tsx
@@ -26,6 +26,10 @@ import SegmentedControl from "../ui/SegmentedControl";
 import Field, { inputClass, selectClass } from "../ui/Field";
 
 
+/** AWS throttles the permission simulator; a check retries patiently instead of failing. */
+export const CHECK_IN_PROGRESS =
+  "Checking permissions… AWS limits how fast this can run, so it can take up to a few minutes.";
+
 const OWN_PRINCIPAL_ACTIONS = ["iam:GetRole", "iam:SimulatePrincipalPolicy"];
 
 const SUMMARY_LABEL: Record<PermissionSummary, string> = {
@@ -184,6 +188,7 @@ function ConnectionRow({ host }: { host: HostConnection }) {
   const [region, setRegion] = useState(host.kind.default_region);
   const [confirmRemove, setConfirmRemove] = useState(false);
   const [busy, setBusy] = useState(false);
+  const [checking, setChecking] = useState(false);
   const [signingIn, setSigningIn] = useState(false);
   const [report, setReport] = useState<PermissionReport | null>(null);
   const [failure, setFailure] = useState<Failure | null>(null);
@@ -201,6 +206,7 @@ function ConnectionRow({ host }: { host: HostConnection }) {
 
   const runCheck = async () => {
     setBusy(true);
+    setChecking(true);
     setFailure(null);
     try {
       setReport(await checkAwsPermissions(host.id));
@@ -208,6 +214,7 @@ function ConnectionRow({ host }: { host: HostConnection }) {
       setReport(null);
       setFailure({ error: toAwsError(e), retry: runCheck });
     } finally {
+      setChecking(false);
       setBusy(false);
     }
   };
@@ -311,7 +318,11 @@ function ConnectionRow({ host }: { host: HostConnection }) {
           </Button>
         </div>
       )}
-      {busy && !editing && !confirmRemove && <p role="status" className="text-xs text-[var(--text-secondary)]">Working…</p>}
+      {busy && !editing && !confirmRemove && (
+        <p role="status" className="text-xs text-[var(--text-secondary)]">
+          {checking ? CHECK_IN_PROGRESS : "Working…"}
+        </p>
+      )}
       {failure && <ErrorLine failure={failure} onSignIn={signIn} signingIn={signingIn} />}
       {report && <PermissionReportView report={report} />}
       <EnvironmentsPanel connection={host} tier={report?.summary} />