diff --git a/apps/mobile/src/features/settings/EnvironmentRoutesSection.tsx b/apps/mobile/src/features/settings/EnvironmentRoutesSection.tsx
index 012d00737d1df..842965dbf1575 100644
--- a/apps/mobile/src/features/settings/EnvironmentRoutesSection.tsx
+++ b/apps/mobile/src/features/settings/EnvironmentRoutesSection.tsx
@@ -12,7 +12,10 @@ import {
   isLearned,
 } from "@t3tools/client-runtime/connection";
 import { type EnvironmentId, sessionGrantsScope } from "@t3tools/contracts";
-import { AUTH_SCOPE_OPTIONS } from "@t3tools/shared/authScopeOptions";
+import {
+  AUTH_SCOPE_OPTIONS,
+  sessionPermissionsUnavailableMessage,
+} from "@t3tools/shared/authScopeOptions";
 import { AsyncResult } from "effect/reactivity";
 import * as Option from "effect/Option";
 import { useState } from "react";
@@ -163,8 +166,14 @@ export function EnvironmentRoutesSection({
             </>
           ) : (
             <Text className="text-sm text-foreground-muted">
-              Permissions not checked. Connect to this environment to view this session’s
-              permissions.
+              {sessionPermissionsUnavailableMessage({
+                connected: activeRouteId !== null,
+                failed: sessionResult._tag === "Failure",
+                rejected:
+                  sessionResult._tag !== "Failure" &&
+                  !sessionResult.waiting &&
+                  session?.authenticated === false,
+              })}
             </Text>
           )}
         </View>
diff --git a/apps/mobile/src/features/settings/SettingsEnvironmentDetailRouteScreen.tsx b/apps/mobile/src/features/settings/SettingsEnvironmentDetailRouteScreen.tsx
index cd9d8e03c9c1f..c581cbc688142 100644
--- a/apps/mobile/src/features/settings/SettingsEnvironmentDetailRouteScreen.tsx
+++ b/apps/mobile/src/features/settings/SettingsEnvironmentDetailRouteScreen.tsx
@@ -8,6 +8,7 @@ import {
   type ServerProvider,
 } from "@t3tools/contracts";
 import { settlePromise, squashAtomCommandFailure } from "@t3tools/client-runtime/state/runtime";
+import { sessionPermissionsUnavailableMessage } from "@t3tools/shared/authScopeOptions";
 import * as Cause from "effect/Cause";
 import * as Exit from "effect/Exit";
 import { AsyncResult } from "effect/reactivity";
@@ -208,11 +209,14 @@ function EnvironmentDetail({ environmentId }: { readonly environmentId: Environm
               </Text>
             ) : !allowed ? (
               <Text className="px-2 text-sm text-foreground-muted">
-                {AsyncResult.isFailure(sessionResult)
-                  ? "Could not verify your permissions. Reconnect to try again."
-                  : session === null
-                    ? "Checking permissions…"
-                    : "This connection does not have permission to manage the environment."}
+                {AsyncResult.isFailure(sessionResult) || session === null || !session.authenticated
+                  ? sessionPermissionsUnavailableMessage({
+                      connected,
+                      failed: AsyncResult.isFailure(sessionResult),
+                      rejected:
+                        !AsyncResult.isFailure(sessionResult) && session?.authenticated === false,
+                    })
+                  : "This connection does not have permission to manage the environment."}
               </Text>
             ) : null}
             {error ? (
diff --git a/apps/web/src/components/settings/SessionPermissions.tsx b/apps/web/src/components/settings/SessionPermissions.tsx
index 1cbff3d750cf3..30f61ddd80371 100644
--- a/apps/web/src/components/settings/SessionPermissions.tsx
+++ b/apps/web/src/components/settings/SessionPermissions.tsx
@@ -1,5 +1,8 @@
 import { type EnvironmentId, sessionGrantsScope } from "@t3tools/contracts";
-import { AUTH_SCOPE_OPTIONS } from "@t3tools/shared/authScopeOptions";
+import {
+  AUTH_SCOPE_OPTIONS,
+  sessionPermissionsUnavailableMessage,
+} from "@t3tools/shared/authScopeOptions";
 import { useEnvironmentSessionState } from "~/state/session";
 
 export function SessionPermissions({
@@ -32,7 +35,11 @@ export function SessionPermissions({
     </div>
   ) : (
     <p className="py-3 text-xs text-muted-foreground">
-      Permissions not checked. Connect to this environment to view this session’s permissions.
+      {sessionPermissionsUnavailableMessage({
+        connected,
+        failed: session.hasError,
+        rejected: !session.hasError && !session.isPending && session.data?.authenticated === false,
+      })}
     </p>
   );
 }
diff --git a/packages/client-runtime/src/state/session.test.ts b/packages/client-runtime/src/state/session.test.ts
new file mode 100644
index 0000000000000..740ab2229bdb4
--- /dev/null
+++ b/packages/client-runtime/src/state/session.test.ts
@@ -0,0 +1,133 @@
+import { describe, expect, it } from "@effect/vitest";
+import { EnvironmentId, type AuthSessionState } from "@t3tools/contracts";
+import * as Clock from "effect/Clock";
+import * as Effect from "effect/Effect";
+import * as Layer from "effect/Layer";
+import * as Option from "effect/Option";
+import * as Queue from "effect/Queue";
+import * as Stream from "effect/Stream";
+import * as SubscriptionRef from "effect/SubscriptionRef";
+import * as TestClock from "effect/testing/TestClock";
+import { AsyncResult, Atom, AtomRegistry } from "effect/reactivity";
+
+import {
+  AVAILABLE_CONNECTION_STATE,
+  PrimaryConnectionTarget,
+  type PreparedConnection,
+} from "../connection/model.ts";
+import * as EnvironmentRegistry from "../connection/registry.ts";
+import * as EnvironmentSupervisor from "../connection/supervisor.ts";
+import * as RpcHttp from "../rpc/http.ts";
+import type { RpcSession } from "../rpc/session.ts";
+import { createEnvironmentSessionAtoms } from "./session.ts";
+
+const TARGET = new PrimaryConnectionTarget({
+  environmentId: EnvironmentId.make("environment-1"),
+  label: "Test environment",
+  httpBaseUrl: "https://environment.example.test",
+  wsBaseUrl: "wss://environment.example.test",
+});
+const PREPARED: PreparedConnection = {
+  environmentId: TARGET.environmentId,
+  label: TARGET.label,
+  httpBaseUrl: "https://environment.example.test",
+  socketUrl: "wss://environment.example.test/ws",
+  httpAuthorization: { _tag: "Bearer", token: "bearer-token" },
+  target: TARGET,
+};
+const SESSION = {
+  authenticated: true,
+  auth: {
+    policy: "remote-reachable",
+    bootstrapMethods: [],
+    sessionMethods: [],
+    sessionCookieName: "t3_session",
+  },
+  scopes: ["orchestration:read"],
+} satisfies AuthSessionState;
+
+const rpcSession = (): RpcSession => ({ closed: Effect.never }) as unknown as RpcSession;
+
+const makeHarness = Effect.fn("TestSessionState.makeHarness")(function* (
+  reply: (requestNumber: number) => Promise<Response>,
+) {
+  let requestCount = 0;
+  const transport = yield* SubscriptionRef.make(Option.some(rpcSession()));
+  const supervisor = EnvironmentSupervisor.EnvironmentSupervisor.of({
+    target: TARGET,
+    state: yield* SubscriptionRef.make(AVAILABLE_CONNECTION_STATE),
+    session: transport,
+    prepared: yield* SubscriptionRef.make(Option.some(PREPARED)),
+    connect: Effect.void,
+    disconnect: Effect.void,
+    retryNow: Effect.void,
+  } satisfies EnvironmentSupervisor.EnvironmentSupervisor["Service"]);
+  const followStream: EnvironmentRegistry.EnvironmentRegistry["Service"]["followStream"] = (
+    _environmentId,
+    stream,
+  ) => Stream.provideService(stream, EnvironmentSupervisor.EnvironmentSupervisor, supervisor);
+  const runtime = Atom.runtime(
+    Layer.mergeAll(
+      Layer.succeed(
+        EnvironmentRegistry.EnvironmentRegistry,
+        EnvironmentRegistry.EnvironmentRegistry.of({
+          followStream,
+        } as unknown as EnvironmentRegistry.EnvironmentRegistry["Service"]),
+      ),
+      RpcHttp.layerRemoteHttpClient(async () => reply(++requestCount)),
+      // The test's clock, so the retry wait moves with `TestClock.adjust`.
+      Layer.succeed(Clock.Clock, yield* Clock.Clock),
+    ),
+  );
+  const registry = yield* Effect.acquireRelease(Effect.sync(AtomRegistry.make), (registry) =>
+    Effect.sync(() => registry.dispose()),
+  );
+  const results = yield* Queue.unbounded<AsyncResult.AsyncResult<AuthSessionState, unknown>>();
+  const atom = createEnvironmentSessionAtoms(runtime).sessionStateAtom(TARGET.environmentId);
+  const unsubscribe = registry.subscribe(atom, (result) => Queue.offerUnsafe(results, result), {
+    immediate: true,
+  });
+  yield* Effect.addFinalizer(() => Effect.sync(unsubscribe));
+  const nextSettled = Effect.fn("TestSessionState.nextSettled")(function* () {
+    for (;;) {
+      const result = yield* Queue.take(results);
+      if (!result.waiting && result._tag !== "Initial") return result;
+    }
+  });
+  return { transport, nextSettled };
+});
+
+const unreachable = () => Promise.reject(new TypeError("Network request failed"));
+
+describe("environment session state", () => {
+  it.effect("fetches permissions again when the connection is re-established", () =>
+    Effect.gen(function* () {
+      const harness = yield* makeHarness((requestNumber) =>
+        requestNumber === 1 ? unreachable() : Promise.resolve(Response.json(SESSION)),
+      );
+      expect((yield* harness.nextSettled())._tag).toBe("Failure");
+
+      yield* SubscriptionRef.set(harness.transport, Option.some(rpcSession()));
+
+      expect(yield* harness.nextSettled()).toMatchObject({ _tag: "Success", value: SESSION });
+    }),
+  );
+
+  it.effect("retries a failed permission check with backoff that restarts per connection", () =>
+    Effect.gen(function* () {
+      const harness = yield* makeHarness((requestNumber) =>
+        requestNumber <= 3 ? unreachable() : Promise.resolve(Response.json(SESSION)),
+      );
+      expect((yield* harness.nextSettled())._tag).toBe("Failure");
+
+      yield* TestClock.adjust("2 seconds");
+      expect((yield* harness.nextSettled())._tag).toBe("Failure");
+
+      yield* SubscriptionRef.set(harness.transport, Option.some(rpcSession()));
+      expect((yield* harness.nextSettled())._tag).toBe("Failure");
+
+      yield* TestClock.adjust("2 seconds");
+      expect(yield* harness.nextSettled()).toMatchObject({ _tag: "Success", value: SESSION });
+    }),
+  );
+});
diff --git a/packages/client-runtime/src/state/session.ts b/packages/client-runtime/src/state/session.ts
index efdf0b37c0a09..90afa29f9d05d 100644
--- a/packages/client-runtime/src/state/session.ts
+++ b/packages/client-runtime/src/state/session.ts
@@ -14,6 +14,7 @@ import type { PreparedConnection } from "../connection/model.ts";
 import * as EnvironmentSupervisor from "../connection/supervisor.ts";
 import * as ManagedRelay from "../relay/managedRelay.ts";
 import type { RemoteEnvironmentRequestError } from "../rpc/http.ts";
+import type { RpcSession } from "../rpc/session.ts";
 import { safeErrorLogAttributes } from "../errors/safeLog.ts";
 import { executeAuthenticatedEnvironmentHttpRequest } from "./environmentHttpAuth.ts";
 import { followStreamInEnvironment } from "./environmentStreams.ts";
@@ -39,6 +40,8 @@ function initialConfigOption<E>(
 
 const DEFAULT_SESSION_STATE_TIMEOUT_MS = 6_000;
 const MAX_SESSION_STATE_TIMEOUT_MS = 60_000;
+const SESSION_STATE_RETRY_BASE_MS = 2_000;
+const SESSION_STATE_RETRY_MAX_MS = 60_000;
 
 export const fetchEnvironmentSessionState = Effect.fn(
   "clientRuntime.state.fetchEnvironmentSessionState",
@@ -136,13 +139,38 @@ function makeEnvironmentSessionAtoms<R, E>(
     ).pipe(Atom.withLabel(`environment-prepared-connection:${environmentId}`)),
   );
 
-  const sessionStateAtom = Atom.family((environmentId: EnvironmentId) =>
-    runtime
+  const transportSessionAtom = Atom.family((environmentId: EnvironmentId) =>
+    runtime.atom(
+      followStreamInEnvironment(
+        environmentId,
+        Stream.unwrap(
+          EnvironmentSupervisor.EnvironmentSupervisor.pipe(
+            Effect.map((supervisor) => SubscriptionRef.changes(supervisor.session)),
+          ),
+        ),
+      ),
+      { initialValue: Option.none() },
+    ),
+  );
+
+  const sessionStateAtom = Atom.family((environmentId: EnvironmentId) => {
+    let consecutiveFailures = 0;
+    let backoffConnection: RpcSession | null = null;
+    return runtime
       .atom((get) => {
         const prepared = Option.getOrNull(get(preparedConnectionValueAtom(environmentId)));
-        if (prepared === null) {
+        // Each established connection fetches anew, and a failure retries while it stays up,
+        // so a fetch that failed mid-reconnect cannot outlive the socket that recovered.
+        const connection = AsyncResult.getOrElse(get(transportSessionAtom(environmentId)), () =>
+          Option.none(),
+        );
+        if (prepared === null || Option.isNone(connection)) {
           return Effect.never;
         }
+        if (connection.value !== backoffConnection) {
+          backoffConnection = connection.value;
+          consecutiveFailures = 0;
+        }
         return Effect.gen(function* () {
           const signer = yield* Effect.serviceOption(ManagedRelay.ManagedRelayDpopSigner);
           const remoteAuthorization = yield* Effect.serviceOption(
@@ -155,14 +183,31 @@ function makeEnvironmentSessionAtoms<R, E>(
             signer,
             remoteAuthorization,
           }).pipe(Effect.provideService(HttpClient.HttpClient, client.value));
-        });
+        }).pipe(
+          Effect.tap(() =>
+            Effect.sync(() => {
+              consecutiveFailures = 0;
+            }),
+          ),
+          Effect.tapError(() => {
+            const delayMs = Math.min(
+              SESSION_STATE_RETRY_BASE_MS * 2 ** consecutiveFailures,
+              SESSION_STATE_RETRY_MAX_MS,
+            );
+            consecutiveFailures += 1;
+            return Effect.sleep(delayMs).pipe(
+              Effect.andThen(Effect.sync(() => get.refreshSelf())),
+              Effect.forkScoped,
+            );
+          }),
+        );
       })
       .pipe(
         Atom.swr({ staleTime: 30_000, revalidateOnMount: true }),
         Atom.setIdleTTL(5 * 60_000),
         Atom.withLabel(`environment-session-state:${environmentId}`),
-      ),
-  );
+      );
+  });
 
   const sessionStateValueAtom = Atom.family((environmentId: EnvironmentId) =>
     Atom.make(
diff --git a/packages/shared/src/authScopeOptions.ts b/packages/shared/src/authScopeOptions.ts
index d443e50326d28..9a2261a09f3e9 100644
--- a/packages/shared/src/authScopeOptions.ts
+++ b/packages/shared/src/authScopeOptions.ts
@@ -104,3 +104,19 @@ export const AUTH_SCOPE_OPTIONS: ReadonlyArray<{
     description: "Change managed tunnel connectivity.",
   },
 ];
+
+/** Shown instead of the granted scopes while they are unknown, so every surface says the same thing. */
+export function sessionPermissionsUnavailableMessage(input: {
+  readonly connected: boolean;
+  /** The check errored; the client retries it while connected. */
+  readonly failed: boolean;
+  /** The environment answered that this session is not signed in; retrying will not change that. */
+  readonly rejected: boolean;
+}): string {
+  if (!input.connected) return "Connect to this environment to view this session’s permissions.";
+  if (input.rejected)
+    return "This environment did not accept your session. Reconnect to try again.";
+  return input.failed
+    ? "Could not verify your permissions. Retrying automatically."
+    : "Checking permissions…";
+}