diff --git a/CHANGELOG.md b/CHANGELOG.md
index 513f273fbf..acac656635 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -18,6 +18,12 @@
   the socket never reaches a terminal failure. The extension keeps retrying until
   the server is reachable again.
 
+### Fixed
+
+- OAuth sign-in now works on deployments that enforce token scopes. Users signed
+  in with OAuth are asked to sign in again once.
+- Revoke OAuth tokens on logout even when their scopes are outdated.
+
 ## [v1.16.4](https://github.com/coder/vscode-coder/releases/tag/v1.16.4) 2026-09-23
 
 ### Added
diff --git a/src/oauth/authorizer.ts b/src/oauth/authorizer.ts
index b22bb90a70..6d23718a7b 100644
--- a/src/oauth/authorizer.ts
+++ b/src/oauth/authorizer.ts
@@ -6,6 +6,7 @@ import { resolveCoderDashboardUrl } from "../util/uri";
 import {
 	AUTH_GRANT_TYPE,
 	DEFAULT_OAUTH_SCOPES,
+	IF_SUPPORTED_OAUTH_SCOPES,
 	PKCE_CHALLENGE_METHOD,
 	RESPONSE_TYPE,
 	TOKEN_ENDPOINT_AUTH_METHOD,
@@ -213,17 +214,23 @@ export class OAuthAuthorizer implements vscode.Disposable {
 			);
 			if (unsupportedScopes.length > 0) {
 				this.logger.warn(
-					`Requested scopes not in server's supported scopes: ${unsupportedScopes.join(", ")}. Server may still accept them.`,
+					`Requested scopes not in server's supported scopes: ${unsupportedScopes.join(", ")}. Servers that enforce scopes reject the request.`,
 					{ supported_scopes: metadata.scopes_supported },
 				);
 			}
 		}
 
+		const scope = [
+			DEFAULT_OAUTH_SCOPES,
+			...IF_SUPPORTED_OAUTH_SCOPES.filter((s) =>
+				metadata.scopes_supported?.includes(s),
+			),
+		].join(" ");
 		const params = new URLSearchParams({
 			client_id: clientId,
 			response_type: RESPONSE_TYPE,
 			redirect_uri: this.getRedirectUri(),
-			scope: DEFAULT_OAUTH_SCOPES,
+			scope,
 			state,
 			code_challenge: challenge,
 			code_challenge_method: PKCE_CHALLENGE_METHOD,
@@ -240,7 +247,7 @@ export class OAuthAuthorizer implements vscode.Disposable {
 		this.logger.debug("Built OAuth authorization URL:", {
 			client_id: clientId,
 			redirect_uri: this.getRedirectUri(),
-			scope: DEFAULT_OAUTH_SCOPES,
+			scope,
 		});
 
 		return endpoint.toString();
diff --git a/src/oauth/constants.ts b/src/oauth/constants.ts
index 542fa517c9..3f8356c62a 100644
--- a/src/oauth/constants.ts
+++ b/src/oauth/constants.ts
@@ -2,17 +2,24 @@
 export const AUTH_GRANT_TYPE = "authorization_code";
 export const REFRESH_GRANT_TYPE = "refresh_token";
 
-// Minimal scopes required by the VS Code extension
+/**
+ * Scopes the extension and the CLI need. Stored sessions must have all of
+ * them, so adding one signs out users of servers that enforce scopes.
+ */
 export const DEFAULT_OAUTH_SCOPES = [
-	"workspace:read",
-	"workspace:update",
-	"workspace:start",
-	"workspace:ssh",
-	"workspace:application_connect",
-	"template:read",
+	"coder:workspaces.operate",
+	"coder:workspaces.access",
+	"workspace:create",
+	"user:read",
 	"user:read_personal",
 ].join(" ");
 
+/**
+ * Requested only when the server lists them in `scopes_supported`, as servers
+ * reject scopes they don't know. Stored sessions don't need them.
+ */
+export const IF_SUPPORTED_OAUTH_SCOPES = ["inbox_notification:read"];
+
 // OAuth 2.1 Response Types
 export const RESPONSE_TYPE = "code";
 
diff --git a/src/oauth/sessionManager.ts b/src/oauth/sessionManager.ts
index 5ccc122aa5..b435910171 100644
--- a/src/oauth/sessionManager.ts
+++ b/src/oauth/sessionManager.ts
@@ -98,8 +98,7 @@ export class OAuthSessionManager implements vscode.Disposable {
 	/**
 	 * Get stored tokens fresh from secrets manager.
 	 * Always reads from storage to ensure cross-window synchronization.
-	 * Validates that tokens match current deployment URL and have required scopes.
-	 * Invalid tokens are cleared and undefined is returned.
+	 * Returns undefined for tokens of another deployment URL.
 	 */
 	private async getStoredTokens(): Promise<StoredTokens | undefined> {
 		if (!this.deployment) {
@@ -122,19 +121,26 @@ export class OAuthSessionManager implements vscode.Disposable {
 			return undefined;
 		}
 
-		if (!this.hasRequiredScopes(auth.oauth.scope)) {
-			this.logger.warn("Stored tokens have insufficient scopes", {
-				scope: auth.oauth.scope,
-			});
-			return undefined;
-		}
-
 		return {
 			access_token: auth.token,
 			...auth.oauth,
 		};
 	}
 
+	/** Stored tokens, or undefined when they lack a required scope. */
+	private async getTokensWithRequiredScopes(): Promise<
+		StoredTokens | undefined
+	> {
+		const storedTokens = await this.getStoredTokens();
+		if (storedTokens && !this.hasRequiredScopes(storedTokens.scope)) {
+			this.logger.warn("Stored tokens have insufficient scopes", {
+				scope: storedTokens.scope,
+			});
+			return undefined;
+		}
+		return storedTokens;
+	}
+
 	/**
 	 * Clear all refresh-related state: in-flight promise, timer, and listener.
 	 * Aborts any in-flight refresh request to prevent stale token updates.
@@ -186,7 +192,7 @@ export class OAuthSessionManager implements vscode.Disposable {
 			this.refreshTimer = undefined;
 		}
 
-		this.getStoredTokens()
+		this.getTokensWithRequiredScopes()
 			.then((storedTokens) => {
 				if (!storedTokens?.refresh_token) {
 					return;
@@ -262,6 +268,9 @@ export class OAuthSessionManager implements vscode.Disposable {
 	 */
 	private hasRequiredScopes(grantedScope: string): boolean {
 		const grantedScopes = new Set(grantedScope.split(" "));
+		if (grantedScopes.has("coder:all")) {
+			return true;
+		}
 		const requiredScopes = DEFAULT_OAUTH_SCOPES.split(" ");
 
 		for (const required of requiredScopes) {
@@ -331,7 +340,7 @@ export class OAuthSessionManager implements vscode.Disposable {
 		this.deployment = deployment;
 		this.clearRefreshState();
 
-		const storedTokens = await this.getStoredTokens();
+		const storedTokens = await this.getTokensWithRequiredScopes();
 		if (storedTokens) {
 			this.logger.debug("Switching OAuth deployment", deployment);
 		}
@@ -385,7 +394,7 @@ export class OAuthSessionManager implements vscode.Disposable {
 		this.refreshAbortController = abortController;
 
 		try {
-			const storedTokens = await this.getStoredTokens();
+			const storedTokens = await this.getTokensWithRequiredScopes();
 			if (!storedTokens?.refresh_token) {
 				throw new Error("No refresh token available");
 			}
@@ -475,6 +484,7 @@ export class OAuthSessionManager implements vscode.Disposable {
 
 	/** Best-effort server-side revocation of the stored refresh and access tokens; never throws. */
 	public async revokeTokens(): Promise<void> {
+		// Includes tokens lacking a required scope, which still work on the server.
 		const storedTokens = await this.getStoredTokens().catch((error) => {
 			this.logger.warn("Failed to read stored tokens for revocation:", error);
 			return undefined;
@@ -535,7 +545,7 @@ export class OAuthSessionManager implements vscode.Disposable {
 		if (hostname && hostname !== this.deployment?.safeHostname) {
 			return false;
 		}
-		const storedTokens = await this.getStoredTokens();
+		const storedTokens = await this.getTokensWithRequiredScopes();
 		return storedTokens !== undefined;
 	}
 
diff --git a/src/oauth/utils.ts b/src/oauth/utils.ts
index a61226ed66..1c65818ea5 100644
--- a/src/oauth/utils.ts
+++ b/src/oauth/utils.ts
@@ -1,7 +1,5 @@
 import { createHash, randomBytes } from "node:crypto";
 
-import { DEFAULT_OAUTH_SCOPES } from "./constants";
-
 import type { OAuth2TokenResponse } from "coder/site/src/api/typesGenerated";
 
 import type { OAuthTokenData } from "../core/secretsManager";
@@ -68,8 +66,8 @@ export function buildOAuthTokenData(
 
 	return {
 		refresh_token: tokenResponse.refresh_token,
-		// Use default scopes when server returns empty, so scope changes can invalidate tokens
-		scope: tokenResponse.scope || DEFAULT_OAUTH_SCOPES,
+		// Servers that ignore scopes return none and grant everything
+		scope: tokenResponse.scope || "coder:all",
 		expiry_timestamp: getExpiryTimestamp(tokenResponse),
 	};
 }
diff --git a/test/unit/oauth/authorizer.test.ts b/test/unit/oauth/authorizer.test.ts
index 2f95f7ae8c..34549bcb61 100644
--- a/test/unit/oauth/authorizer.test.ts
+++ b/test/unit/oauth/authorizer.test.ts
@@ -4,6 +4,10 @@ import * as vscode from "vscode";
 import { InvalidApiResponseError } from "@/api/responseValidation";
 import { getHeaders } from "@/headers";
 import { OAuthAuthorizer } from "@/oauth/authorizer";
+import {
+	DEFAULT_OAUTH_SCOPES,
+	IF_SUPPORTED_OAUTH_SCOPES,
+} from "@/oauth/constants";
 
 import {
 	createMockUser,
@@ -372,6 +376,27 @@ describe("OAuthAuthorizer", () => {
 			await completeLogin(state);
 			await loginPromise;
 		});
+
+		it.each([
+			{ name: "the server supports", supported: IF_SUPPORTED_OAUTH_SCOPES },
+			{ name: "none when the server supports none", supported: [] },
+		])("requests IF_SUPPORTED_OAUTH_SCOPES: $name", async ({ supported }) => {
+			const { setupOAuthRoutes, startLogin, completeLogin } =
+				createTestContext();
+			setupOAuthRoutes(
+				createMockOAuthMetadata(TEST_URL, {
+					scopes_supported: [...DEFAULT_OAUTH_SCOPES.split(" "), ...supported],
+				}),
+			);
+
+			const { loginPromise, authUrl, state } = await startLogin();
+			expect(authUrl.searchParams.get("scope")).toBe(
+				[DEFAULT_OAUTH_SCOPES, ...supported].join(" "),
+			);
+
+			await completeLogin(state);
+			await loginPromise;
+		});
 	});
 
 	describe("callback handling", () => {
diff --git a/test/unit/oauth/sessionManager.test.ts b/test/unit/oauth/sessionManager.test.ts
index b02927fc4a..34608e2fc1 100644
--- a/test/unit/oauth/sessionManager.test.ts
+++ b/test/unit/oauth/sessionManager.test.ts
@@ -484,6 +484,19 @@ describe("OAuthSessionManager", () => {
 			]);
 		});
 
+		it("revokes tokens with outdated scopes", async () => {
+			const { manager, setupForOAuthOperation } = createTestContext();
+			const revoke = vi.fn(() => ({}));
+			await setupForOAuthOperation(
+				{ "/oauth2/revoke": revoke },
+				{ scope: "workspace:read" },
+			);
+
+			await manager.revokeTokens();
+
+			expect(revoke).toHaveBeenCalledTimes(2);
+		});
+
 		it("does not throw when revocation fails", async () => {
 			const { manager, setupForOAuthOperation } = createTestContext();
 
@@ -531,14 +544,22 @@ describe("OAuthSessionManager", () => {
 				oauth: {
 					refresh_token: "refresh-token",
 					expiry_timestamp: Date.now() + ONE_HOUR_MS,
-					// workspace:* covers workspace:read, workspace:update, etc.
-					scope: "workspace:* template:read user:read_personal",
+					// workspace:* and user:* cover the low-level scopes
+					scope:
+						"coder:workspaces.operate coder:workspaces.access workspace:* user:*",
 				},
 			});
 
 			const result = await manager.isLoggedInWithOAuth();
 			expect(result).toBe(true);
 		});
+
+		it("accepts coder:all", async () => {
+			const { manager, setupOAuthSession } = createTestContext();
+			await setupOAuthSession({ scope: "coder:all" });
+
+			expect(await manager.isLoggedInWithOAuth()).toBe(true);
+		});
 	});
 
 	describe("telemetry", () => {
diff --git a/test/unit/oauth/testUtils.ts b/test/unit/oauth/testUtils.ts
index 8729aa4291..f12954b82b 100644
--- a/test/unit/oauth/testUtils.ts
+++ b/test/unit/oauth/testUtils.ts
@@ -64,12 +64,10 @@ export function createMockOAuthMetadata(
 		revocation_endpoint: `${issuer}/oauth2/revoke`,
 		registration_endpoint: `${issuer}/oauth2/register`,
 		scopes_supported: [
-			"workspace:read",
-			"workspace:update",
-			"workspace:start",
-			"workspace:ssh",
-			"workspace:application_connect",
-			"template:read",
+			"coder:workspaces.operate",
+			"coder:workspaces.access",
+			"workspace:create",
+			"user:read",
 			"user:read_personal",
 		],
 		response_types_supported: ["code"],
diff --git a/test/unit/oauth/utils.test.ts b/test/unit/oauth/utils.test.ts
index 4dafa024ba..1bebaf8e95 100644
--- a/test/unit/oauth/utils.test.ts
+++ b/test/unit/oauth/utils.test.ts
@@ -147,6 +147,12 @@ describe("buildOAuthTokenData", () => {
 		});
 	});
 
+	it("stores coder:all when the server returns no scope", () => {
+		expect(
+			buildOAuthTokenData(createTokenResponse({ scope: undefined })).scope,
+		).toBe("coder:all");
+	});
+
 	describe("token_type validation", () => {
 		it("accepts Bearer tokens", () => {
 			expect(() =>