diff --git a/components/dashboard/src/Login.tsx b/components/dashboard/src/Login.tsx
index e67bca5f2024de..71df482bdecef1 100644
--- a/components/dashboard/src/Login.tsx
+++ b/components/dashboard/src/Login.tsx
@@ -53,7 +53,7 @@ export function Login() {
     }, [])
 
     const authorizeSuccessful = async (payload?: string) => {
-        updateUser();
+        updateUser().catch(console.error);
         // Check for a valid returnTo in payload
         const safeReturnTo = getSafeURLRedirect(payload);
         if (safeReturnTo) {
diff --git a/components/gitpod-protocol/src/messaging/browser/connection.ts b/components/gitpod-protocol/src/messaging/browser/connection.ts
index 9adc452a7795da..3b495b6123b2a2 100644
--- a/components/gitpod-protocol/src/messaging/browser/connection.ts
+++ b/components/gitpod-protocol/src/messaging/browser/connection.ts
@@ -5,10 +5,13 @@
  * You may obtain a copy of the License at http://www.apache.org/licenses/LICENSE-2.0
  */
 
-import { listen as doListen, Logger, ConsoleLogger } from "vscode-ws-jsonrpc";
+import { Logger, ConsoleLogger, toSocket, IWebSocket } from "vscode-ws-jsonrpc";
+import { MessageConnection, createMessageConnection } from "vscode-jsonrpc";
+import { AbstractMessageWriter } from "vscode-jsonrpc/lib/messageWriter";
+import { AbstractMessageReader } from "vscode-jsonrpc/lib/messageReader";
 import { JsonRpcProxyFactory, JsonRpcProxy } from "../proxy-factory";
 import { ConnectionHandler } from "../handler";
-import ReconnectingWebSocket from 'reconnecting-websocket';
+import ReconnectingWebSocket, { Event } from 'reconnecting-websocket';
 
 export interface WebSocketOptions {
     onerror?: (event: Event) => void;
@@ -64,11 +67,11 @@ export class WebSocketConnectionProvider {
                 logger.error(JSON.stringify(error));
             });
         }
-        doListen({
-            webSocket,
-            onConnection: connection => handler.onConnection(connection),
-            logger
-        });
+        doListen(
+            webSocket as any as ReconnectingWebSocket,
+            connection => handler.onConnection(connection),
+            logger,
+        );
         return webSocket;
     }
 
@@ -91,3 +94,156 @@ export class WebSocketConnectionProvider {
     }
 
 }
+
+// The following was extracted from vscode-ws-jsonrpc to make these changes:
+//  - switch from WebSocket to ReconnectingWebSocket
+//  - webSocket.onopen: making sure it's only ever called once so we're re-using MessageConnection
+//  - WebSocketMessageWriter: buffer and re-try messages instead of throwing an error immidiately
+//  - WebSocketMessageReader: don't close MessageConnection on 'socket.onclose'
+function doListen(resocket: ReconnectingWebSocket, onConnection: (connection: MessageConnection) => void, logger: Logger) {
+    let alreadyOpened = false;
+    resocket.onopen = () => {
+        if (alreadyOpened) {
+            return;
+        }
+        alreadyOpened = true;
+
+        const connection = createWebSocketConnection(resocket, logger);
+        onConnection(connection);
+    };
+}
+
+function createWebSocketConnection(resocket: ReconnectingWebSocket, logger: Logger) {
+    const socket = toSocket(resocket as any);
+    const messageReader = new NonClosingWebSocketMessageReader(socket);
+    const messageWriter = new BufferingWebSocketMessageWriter(resocket, logger);
+    const connection = createMessageConnection(messageReader, messageWriter, logger);
+    connection.onClose(() => connection.dispose());
+    return connection;
+}
+
+/**
+ * This takes vscode-ws-jsonrpc/lib/socket/writer/WebSocketMessageWriter and adds a buffer
+ */
+class BufferingWebSocketMessageWriter extends AbstractMessageWriter {
+    protected readonly socket: ReconnectingWebSocket;
+    protected readonly logger: Logger;
+    protected errorCount: number = 0;
+
+    protected buffer: any[] = [];
+
+    constructor(socket: ReconnectingWebSocket, logger: Logger) {
+        super();
+        this.socket = socket;
+        this.logger = logger;
+
+        socket.addEventListener("open", (event: Event) => this.flushBuffer());
+    }
+
+    write(msg: any) {
+        if (this.socket.readyState !== ReconnectingWebSocket.OPEN) {
+            this.bufferMsg(msg);
+            return;
+        }
+
+        try {
+            const content = JSON.stringify(msg);
+            this.socket.send(content);
+        } catch (e) {
+            this.errorCount++;
+            this.fireError(e, msg, this.errorCount);
+
+            this.bufferMsg(msg);
+        }
+    }
+
+    protected flushBuffer() {
+        if (this.buffer.length === 0) {
+            return
+        }
+
+        const buffer = [...this.buffer];
+        this.buffer = [];
+        for (const msg of buffer) {
+            this.write(msg);
+        }
+        this.logger.info(`flushed buffer (${this.buffer.length})`)
+    }
+
+    protected bufferMsg(msg: any) {
+        this.buffer.push(msg);
+        this.logger.info(`buffered message (${this.buffer.length})`);
+    }
+}
+
+
+/**
+ * This takes vscode-ws-jsonrpc/lib/socket/reader/WebSocketMessageReader and removes the "onClose -> fireClose" connection
+ */
+class NonClosingWebSocketMessageReader extends AbstractMessageReader {
+    protected readonly socket: IWebSocket;
+    protected readonly events: any[] = [];
+    protected state: 'initial' | 'listening' | 'closed' = 'initial';
+    protected callback: (message: any) => void = () => {};
+
+    constructor(socket: IWebSocket) {
+        super();
+        this.socket = socket;
+        this.socket.onMessage(message => this.readMessage(message));
+        this.socket.onError(error => this.fireError(error));
+        this.socket.onClose((code, reason) => {
+            if (code !== 1000) {
+                const error = {
+                    name: '' + code,
+                    message: `Error during socket reconnect: code = ${code}, reason = ${reason}`
+                };
+                this.fireError(error);
+            }
+            // this.fireClose();        // <-- reason for this class to be copied over
+        });
+    }
+    listen(callback: (message: any) => void) {
+        if (this.state === 'initial') {
+            this.state = 'listening';
+            this.callback = callback;
+            while (this.events.length !== 0) {
+                const event = this.events.pop();
+                if (event.message) {
+                    this.readMessage(event.message);
+                }
+                else if (event.error) {
+                    this.fireError(event.error);
+                }
+                else {
+                    this.fireClose();
+                }
+            }
+        }
+    }
+    readMessage(message: any) {
+        if (this.state === 'initial') {
+            this.events.splice(0, 0, { message });
+        }
+        else if (this.state === 'listening') {
+            const data = JSON.parse(message);
+            this.callback(data);
+        }
+    }
+    fireError(error: any) {
+        if (this.state === 'initial') {
+            this.events.splice(0, 0, { error });
+        }
+        else if (this.state === 'listening') {
+            super.fireError(error);
+        }
+    }
+    fireClose() {
+        if (this.state === 'initial') {
+            this.events.splice(0, 0, {});
+        }
+        else if (this.state === 'listening') {
+            super.fireClose();
+        }
+        this.state = 'closed';
+    }
+}