diff --git a/src/commands.ts b/src/commands.ts
index 19daaa57..b0024316 100644
--- a/src/commands.ts
+++ b/src/commands.ts
@@ -86,7 +86,7 @@ export class Commands {
 		if (this.deploymentManager.isAuthenticated()) {
 			return;
 		}
-		this.logger.info("Logging in");
+		this.logger.debug("Logging in");
 
 		const currentDeployment = await this.secretsManager.getCurrentDeployment();
 		const url = await maybeAskUrl(
@@ -205,7 +205,7 @@ export class Commands {
 			return;
 		}
 
-		this.logger.info("Logging out");
+		this.logger.debug("Logging out");
 
 		await this.deploymentManager.clearDeployment();
 
diff --git a/src/deployment/deploymentManager.ts b/src/deployment/deploymentManager.ts
index 8bb34629..4922d5a3 100644
--- a/src/deployment/deploymentManager.ts
+++ b/src/deployment/deploymentManager.ts
@@ -7,7 +7,11 @@ import { type Logger } from "../logging/logger";
 import { type OAuthSessionManager } from "../oauth/sessionManager";
 import { type WorkspaceProvider } from "../workspace/workspacesProvider";
 
-import { type Deployment, type DeploymentWithAuth } from "./types";
+import {
+	DeploymentSchema,
+	type Deployment,
+	type DeploymentWithAuth,
+} from "./types";
 
 import type { User } from "coder/site/src/api/typesGenerated";
 import type * as vscode from "vscode";
@@ -115,6 +119,10 @@ export class DeploymentManager implements vscode.Disposable {
 	public async setDeployment(
 		deployment: DeploymentWithAuth & { user: User },
 	): Promise<void> {
+		this.logger.debug("Setting deployment", {
+			hostname: deployment.safeHostname,
+			user: deployment.user.username,
+		});
 		this.#deployment = { ...deployment };
 
 		// Updates client credentials
@@ -131,14 +139,17 @@ export class DeploymentManager implements vscode.Disposable {
 		this.updateAuthContexts(deployment.user);
 		this.refreshWorkspaces();
 
-		await this.oauthSessionManager.setDeployment(deployment);
-		await this.persistDeployment(deployment);
+		const deploymentWithoutAuth: Deployment =
+			DeploymentSchema.parse(deployment);
+		await this.oauthSessionManager.setDeployment(deploymentWithoutAuth);
+		await this.persistDeployment(deploymentWithoutAuth);
 	}
 
 	/**
 	 * Clears the current deployment.
 	 */
 	public async clearDeployment(): Promise<void> {
+		this.logger.debug("Clearing deployment", this.#deployment?.safeHostname);
 		this.suspendSession();
 		this.#authListenerDisposable?.dispose();
 		this.#authListenerDisposable = undefined;
diff --git a/src/login/loginCoordinator.ts b/src/login/loginCoordinator.ts
index 1abb342c..a065d534 100644
--- a/src/login/loginCoordinator.ts
+++ b/src/login/loginCoordinator.ts
@@ -367,7 +367,7 @@ export class LoginCoordinator implements vscode.Disposable {
 	 */
 	private async loginWithOAuth(deployment: Deployment): Promise<LoginResult> {
 		try {
-			this.logger.info("Starting OAuth authentication");
+			this.logger.debug("Starting OAuth authentication");
 
 			const { tokenResponse, user } = await vscode.window.withProgress(
 				{
diff --git a/src/oauth/authorizer.ts b/src/oauth/authorizer.ts
index 001c06c7..98e2a119 100644
--- a/src/oauth/authorizer.ts
+++ b/src/oauth/authorizer.ts
@@ -96,7 +96,7 @@ export class OAuthAuthorizer implements vscode.Disposable {
 		reportProgress("fetching user...", 20);
 		const user = await client.getAuthenticatedUser();
 
-		this.logger.info("OAuth login flow completed successfully");
+		this.logger.debug("OAuth login flow completed successfully");
 
 		return {
 			tokenResponse,
@@ -157,7 +157,7 @@ export class OAuthAuthorizer implements vscode.Disposable {
 			deployment.safeHostname,
 			response.data,
 		);
-		this.logger.info(
+		this.logger.debug(
 			"Saved OAuth client registration:",
 			response.data.client_id,
 		);
diff --git a/src/oauth/sessionManager.ts b/src/oauth/sessionManager.ts
index a073173f..32ab7e78 100644
--- a/src/oauth/sessionManager.ts
+++ b/src/oauth/sessionManager.ts
@@ -311,12 +311,15 @@ export class OAuthSessionManager implements vscode.Disposable {
 		) {
 			return;
 		}
-		this.logger.debug("Switching OAuth deployment", deployment);
 		this.deployment = deployment;
 		this.clearRefreshState();
 
-		// Block on refresh if token is expired to ensure valid state for callers
 		const storedTokens = await this.getStoredTokens();
+		if (storedTokens) {
+			this.logger.debug("Switching OAuth deployment", deployment);
+		}
+
+		// Block on refresh if token is expired to ensure valid state for callers
 		if (storedTokens && Date.now() >= storedTokens.expiry_timestamp) {
 			try {
 				await this.refreshToken();
@@ -331,7 +334,6 @@ export class OAuthSessionManager implements vscode.Disposable {
 	}
 
 	public clearDeployment(): void {
-		this.logger.debug("Clearing OAuth deployment state");
 		this.deployment = null;
 		this.clearRefreshState();
 	}
@@ -422,7 +424,7 @@ export class OAuthSessionManager implements vscode.Disposable {
 	public async revokeRefreshToken(): Promise<void> {
 		const storedTokens = await this.getStoredTokens();
 		if (!storedTokens?.refresh_token) {
-			this.logger.info("No refresh token to revoke");
+			this.logger.debug("No refresh token to revoke");
 			return;
 		}
 
@@ -449,11 +451,13 @@ export class OAuthSessionManager implements vscode.Disposable {
 			await this.prepareOAuthOperation(authToken);
 
 		if (!metadata.revocation_endpoint) {
-			this.logger.info("No revocation endpoint available, skipping revocation");
+			this.logger.debug(
+				"No revocation endpoint available, skipping revocation",
+			);
 			return;
 		}
 
-		this.logger.info("Revoking refresh token");
+		this.logger.debug("Revoking refresh token");
 
 		const params: OAuth2TokenRevocationRequest = {
 			token: tokenToRevoke,
@@ -475,7 +479,7 @@ export class OAuthSessionManager implements vscode.Disposable {
 				},
 			);
 
-			this.logger.info("Token revocation successful");
+			this.logger.debug("Token revocation successful");
 		} catch (error) {
 			this.logger.error("Token revocation failed:", error);
 			throw error;
@@ -503,6 +507,5 @@ export class OAuthSessionManager implements vscode.Disposable {
 	public dispose(): void {
 		this.disposed = true;
 		this.clearDeployment();
-		this.logger.debug("OAuth session manager disposed");
 	}
 }
diff --git a/src/remote/remote.ts b/src/remote/remote.ts
index 8dab3c3c..7dcdce41 100644
--- a/src/remote/remote.ts
+++ b/src/remote/remote.ts
@@ -101,6 +101,12 @@ export class Remote {
 			return;
 		}
 
+		this.logger.debug("Setting up remote connection", {
+			hostname: parts.safeHostname,
+			workspace: `${parts.username}/${parts.workspace}`,
+			agent: parts.agent || "(default)",
+		});
+
 		const workspaceName = `${parts.username}/${parts.workspace}`;
 
 		// Migrate existing legacy file-based auth to secrets storage.
@@ -110,6 +116,11 @@ export class Remote {
 		const auth = await this.secretsManager.getSessionAuth(parts.safeHostname);
 		const baseUrlRaw = auth?.url ?? "";
 		const token = auth?.token;
+		this.logger.debug("Retrieved auth for hostname", {
+			hostname: parts.safeHostname,
+			hasUrl: Boolean(baseUrlRaw),
+			hasToken: token !== undefined,
+		});
 		// Empty token is valid for mTLS
 		if (baseUrlRaw && token !== undefined) {
 			await this.cliManager.configure(parts.safeHostname, baseUrlRaw, token);
@@ -343,6 +354,10 @@ export class Remote {
 			);
 
 			// Wait for workspace to be running and agent to be ready
+			this.logger.debug("Starting workspace state machine", {
+				workspace: workspaceName,
+				initialStatus: workspace.latest_build.status,
+			});
 			const stateMachine = new WorkspaceStateMachine(
 				parts,
 				workspaceClient,
@@ -423,6 +438,12 @@ export class Remote {
 				throw new Error("Failed to get workspace or agent from state machine");
 			}
 
+			this.logger.info("Workspace ready", {
+				workspace: workspaceName,
+				agent: agent.name,
+				status: workspace.latest_build.status,
+			});
+
 			this.commands.workspace = workspace;
 
 			// Watch coder inbox for messages
diff --git a/src/workspace/workspacesProvider.ts b/src/workspace/workspacesProvider.ts
index a8d19ffc..ff462e75 100644
--- a/src/workspace/workspacesProvider.ts
+++ b/src/workspace/workspacesProvider.ts
@@ -101,11 +101,9 @@ export class WorkspaceProvider
 	 * logged in or the query fails.
 	 */
 	private async fetch(): Promise<WorkspaceTreeItem[]> {
-		if (vscode.env.logLevel <= vscode.LogLevel.Debug) {
-			this.logger.info(
-				`Fetching workspaces: ${this.getWorkspacesQuery || "no filter"}...`,
-			);
-		}
+		this.logger.debug(
+			`Fetching workspaces: ${this.getWorkspacesQuery || "no filter"}...`,
+		);
 
 		// If there is no URL configured, assume we are logged out.
 		const url = this.client.getAxiosInstance().defaults.baseURL;