diff --git a/packages/ide/src/fill/notification.ts b/packages/ide/src/fill/notification.ts
index ebda3eeea..f1c156c9f 100644
--- a/packages/ide/src/fill/notification.ts
+++ b/packages/ide/src/fill/notification.ts
@@ -41,20 +41,30 @@ export interface IProgressService {
 }
 
 /**
- * Temporary notification service.
+ * Console-based notification service.
  */
 export class NotificationService implements INotificationService {
 	public error(error: Error): void {
 		logger.error(error.message, field("error", error));
 	}
 
-	public prompt(_severity: Severity, message: string, _buttons: INotificationButton[], _onCancel: () => void): INotificationHandle {
-		throw new Error(`cannot prompt using the console: ${message}`);
+	public prompt(severity: Severity, message: string, _buttons: INotificationButton[], _onCancel: () => void): INotificationHandle {
+		switch (severity) {
+			case Severity.Info: logger.info(message); break;
+			case Severity.Warning: logger.warn(message); break;
+			case Severity.Error: logger.error(message); break;
+		}
+
+		return {
+			close: (): void => undefined,
+			updateMessage: (): void => undefined,
+			updateButtons: (): void => undefined,
+		};
 	}
 }
 
 /**
- * Temporary progress service.
+ * Console-based progress service.
  */
 export class ProgressService implements IProgressService {
 	public start<T>(title: string, task: (progress: IProgress) => Promise<T>): Promise<T> {
diff --git a/packages/ide/src/retry.ts b/packages/ide/src/retry.ts
index 2902c0c41..9cf41af31 100644
--- a/packages/ide/src/retry.ts
+++ b/packages/ide/src/retry.ts
@@ -1,4 +1,4 @@
-import { logger } from "@coder/logger";
+import { logger, field } from "@coder/logger";
 import { NotificationService, INotificationHandle, INotificationService, Severity } from "./fill/notification";
 
 interface IRetryItem {
@@ -105,7 +105,7 @@ export class Retry {
 	/**
 	 * Retry a service.
 	 */
-	public run(name: string): void {
+	public run(name: string, error?: Error): void {
 		if (!this.items.has(name)) {
 			throw new Error(`"${name}" is not registered`);
 		}
@@ -117,7 +117,7 @@ export class Retry {
 
 		item.running = true;
 		// This timeout is for the case when the connection drops; this allows time
-		// for the Wush service to come in and block everything because some other
+		// for the socket service to come in and block everything because some other
 		// services might make it here first and try to restart, which will fail.
 		setTimeout(() => {
 			if (this.blocked && this.blocked !== name) {
@@ -125,7 +125,7 @@ export class Retry {
 			}
 
 			if (!item.count || item.count < this.maxImmediateRetries) {
-				return this.runItem(name, item);
+				return this.runItem(name, item, error);
 			}
 
 			if (!item.delay) {
@@ -137,10 +137,10 @@ export class Retry {
 				}
 			}
 
-			logger.info(`Retrying ${name.toLowerCase()} in ${item.delay}s`);
+			logger.info(`Retrying ${name.toLowerCase()} in ${item.delay}s`, error && field("error", error.message));
 			const itemDelayMs = item.delay * 1000;
 			item.end = Date.now() + itemDelayMs;
-			item.timeout = setTimeout(() => this.runItem(name, item), itemDelayMs);
+			item.timeout = setTimeout(() => this.runItem(name, item, error), itemDelayMs);
 
 			this.updateNotification();
 		}, this.waitDelay);
@@ -165,7 +165,7 @@ export class Retry {
 	/**
 	 * Run an item.
 	 */
-	private runItem(name: string, item: IRetryItem): void {
+	private runItem(name: string, item: IRetryItem, error?: Error): void {
 		if (!item.count) {
 			item.count = 1;
 		} else {
@@ -175,7 +175,7 @@ export class Retry {
 		const retryCountText = item.count <= this.maxImmediateRetries
 			? `[${item.count}/${this.maxImmediateRetries}]`
 			: `[${item.count}]`;
-		logger.info(`Trying ${name.toLowerCase()} ${retryCountText}...`);
+		logger.info(`Starting ${name.toLowerCase()} ${retryCountText}...`, error && field("error", error.message));
 
 		const endItem = (): void => {
 			this.stopItem(item);
diff --git a/packages/logger/src/logger.ts b/packages/logger/src/logger.ts
index 0564ff39f..4f3449467 100644
--- a/packages/logger/src/logger.ts
+++ b/packages/logger/src/logger.ts
@@ -38,8 +38,10 @@ export class Time {
 	) { }
 }
 
+// `undefined` is allowed to make it easy to conditionally display a field.
+// For example: `error && field("error", error)`
 // tslint:disable-next-line no-any
-export type FieldArray = Array<Field<any>>;
+export type FieldArray = Array<Field<any> | undefined>;
 
 // Functions can be used to remove the need to perform operations when the
 // logging level won't output the result anyway.
@@ -338,9 +340,9 @@ export class Logger {
 			passedFields = values as FieldArray;
 		}
 
-		const fields = this.defaultFields
-			? passedFields.concat(this.defaultFields)
-			: passedFields;
+		const fields = (this.defaultFields
+			? passedFields.filter((f) => !!f).concat(this.defaultFields)
+			: passedFields.filter((f) => !!f)) as Array<Field<any>>; // tslint:disable-line no-any
 
 		const now = Date.now();
 		let times: Array<Field<Time>> = [];
diff --git a/packages/server/src/cli.ts b/packages/server/src/cli.ts
index 761850888..f0c9dc2e3 100644
--- a/packages/server/src/cli.ts
+++ b/packages/server/src/cli.ts
@@ -92,7 +92,6 @@ export class Entry extends Command {
 		logger.info("Additional documentation: https://coder.com/docs");
 		logger.info("Initializing", field("data-dir", dataDir), field("working-dir", workingDir), field("log-dir", logDir));
 		const sharedProcess = new SharedProcess(dataDir, builtInExtensionsDir);
-		logger.info("Starting shared process...", field("socket", sharedProcess.socketPath));
 		const sendSharedProcessReady = (socket: WebSocket): void => {
 			const active = new SharedProcessActiveMessage();
 			active.setSocketPath(sharedProcess.socketPath);
@@ -102,12 +101,7 @@ export class Entry extends Command {
 			socket.send(serverMessage.serializeBinary());
 		};
 		sharedProcess.onState((event) => {
-			if (event.state === SharedProcessState.Stopped) {
-				logger.error("Shared process stopped. Restarting...", field("error", event.error));
-			} else if (event.state === SharedProcessState.Starting) {
-				logger.info("Starting shared process...");
-			} else if (event.state === SharedProcessState.Ready) {
-				logger.info("Shared process is ready!");
+			if (event.state === SharedProcessState.Ready) {
 				app.wss.clients.forEach((c) => sendSharedProcessReady(c));
 			}
 		});
diff --git a/packages/server/src/vscode/sharedProcess.ts b/packages/server/src/vscode/sharedProcess.ts
index 41e917dae..49d847b5d 100644
--- a/packages/server/src/vscode/sharedProcess.ts
+++ b/packages/server/src/vscode/sharedProcess.ts
@@ -6,7 +6,8 @@ import { forkModule } from "./bootstrapFork";
 import { StdioIpcHandler } from "../ipc";
 import { ParsedArgs } from "vs/platform/environment/common/environment";
 import { LogLevel } from "vs/platform/log/common/log";
-import { Emitter, Event } from "@coder/events/src";
+import { Emitter } from "@coder/events/src";
+import { retry } from "@coder/ide/src/retry";
 
 export enum SharedProcessState {
 	Stopped,
@@ -28,12 +29,14 @@ export class SharedProcess {
 	private ipcHandler: StdioIpcHandler | undefined;
 	private readonly onStateEmitter = new Emitter<SharedProcessEvent>();
 	public readonly onState = this.onStateEmitter.event;
+	private readonly retryName = "Shared process";
 
 	public constructor(
 		private readonly userDataDir: string,
 		private readonly builtInExtensionsDir: string,
 	) {
-		this.restart();
+		retry.register(this.retryName, () => this.restart());
+		retry.run(this.retryName);
 	}
 
 	public get state(): SharedProcessState {
@@ -73,7 +76,7 @@ export class SharedProcess {
 					state: SharedProcessState.Stopped,
 				});
 			}
-			this.restart();
+			retry.run(this.retryName, new Error(`Exited with ${err}`));
 		});
 		this.ipcHandler = new StdioIpcHandler(this.activeProcess);
 		this.ipcHandler.once("handshake:hello", () => {
@@ -94,6 +97,7 @@ export class SharedProcess {
 		});
 		this.ipcHandler.once("handshake:im ready", () => {
 			resolved = true;
+			retry.recover(this.retryName);
 			this.setState({
 				state: SharedProcessState.Ready,
 			});