diff --git a/src/debugAdapter.ts b/src/debugAdapter.ts
index 4b4c48ebbb..8a9184d0c0 100644
--- a/src/debugAdapter.ts
+++ b/src/debugAdapter.ts
@@ -26,49 +26,107 @@ var debugAdapterLogWriter =
 // debug server
 process.stdin.pause();
 
-// Read the details of the current session to learn
-// the connection details for the debug service
-let sessionDetails = utils.readSessionFile();
-
-// Establish connection before setting up the session
-debugAdapterLogWriter.write("Connecting to port: " + sessionDetails.debugServicePort + "\r\n");
-let debugServiceSocket = net.connect(sessionDetails.debugServicePort, '127.0.0.1');
-
-// Write any errors to the log file
-debugServiceSocket.on(
-    'error',
-    (e) => debugAdapterLogWriter.write("Socket connect ERROR: " + e + "\r\n"));
-
-// Route any output from the socket through stdout
-debugServiceSocket.on(
-    'data',
-    (data: Buffer) => process.stdout.write(data));
-
-// Wait for the connection to complete
-debugServiceSocket.on(
-    'connect',
-    () => {
-        debugAdapterLogWriter.write("Connected to socket!\r\n\r\n");
-
-        // When data comes on stdin, route it through the socket
-        process.stdin.on(
-            'data',
-            (data: Buffer) => debugServiceSocket.write(data));
-
-        // Resume the stdin stream
-        process.stdin.resume();
-    });
-
-// When the socket closes, end the session
-debugServiceSocket.on(
-    'close',
-    () => {
-        debugAdapterLogWriter.write("Socket closed, shutting down.");
-
-        // Close after a short delay to give the client time
-        // to finish up
-        setTimeout(() => {
+function startDebugging() {
+    // Read the details of the current session to learn
+    // the connection details for the debug service
+    let sessionDetails = utils.readSessionFile();
+
+    // Establish connection before setting up the session
+    debugAdapterLogWriter.write("Connecting to port: " + sessionDetails.debugServicePort + "\r\n");
+
+    let isConnected = false;
+    let debugServiceSocket = net.connect(sessionDetails.debugServicePort, '127.0.0.1');
+
+    // Write any errors to the log file
+    debugServiceSocket.on(
+        'error',
+        (e) => {
+            debugAdapterLogWriter.write("Socket ERROR: " + e + "\r\n")
+            debugAdapterLogWriter.close();
+            debugServiceSocket.destroy();
             process.exit(0);
-        }, 1000);
+        });
+
+    // Route any output from the socket through stdout
+    debugServiceSocket.on(
+        'data',
+        (data: Buffer) => process.stdout.write(data));
+
+    // Wait for the connection to complete
+    debugServiceSocket.on(
+        'connect',
+        () => {
+            isConnected = true;
+            debugAdapterLogWriter.write("Connected to socket!\r\n\r\n");
+
+            // When data comes on stdin, route it through the socket
+            process.stdin.on(
+                'data',
+                (data: Buffer) => debugServiceSocket.write(data));
+
+            // Resume the stdin stream
+            process.stdin.resume();
+        });
+
+    // When the socket closes, end the session
+    debugServiceSocket.on(
+        'close',
+        () => {
+            debugAdapterLogWriter.write("Socket closed, shutting down.");
+            debugAdapterLogWriter.close();
+            isConnected = false;
+
+            // Close after a short delay to give the client time
+            // to finish up
+            setTimeout(() => {
+                process.exit(0);
+            }, 2000);
+        }
+    )
+
+    process.on(
+        'exit',
+        (e) => {
+            if (debugAdapterLogWriter) {
+                debugAdapterLogWriter.write("Debug adapter process is exiting...");
+            }
+        }
+    )
+}
+
+var sessionFilePath = utils.getSessionFilePath();
+function waitForSessionFile(triesRemaining: number) {
+
+    debugAdapterLogWriter.write(`Waiting for session file, tries remaining: ${triesRemaining}...\r\n`);
+
+    if (triesRemaining > 0) {
+        if (utils.checkIfFileExists(sessionFilePath)) {
+            debugAdapterLogWriter.write(`Session file present, connecting to debug adapter...\r\n\r\n`);
+            startDebugging();
+        }
+        else {
+            // Wait for a second and try again
+            setTimeout(
+                () => waitForSessionFile(triesRemaining - 1),
+                1000);
+        }
+    }
+    else {
+        debugAdapterLogWriter.write(`Timed out waiting for session file!\r\n`);
+        var errorJson =
+            JSON.stringify({
+                type: "response",
+                request_seq: 1,
+                command: "initialize",
+                success: false,
+                message: "Timed out waiting for the PowerShell extension to start."
+            });
+
+        process.stdout.write(
+            `Content-Length: ${Buffer.byteLength(errorJson, 'utf8')}\r\n\r\n${errorJson}`,
+            'utf8');
     }
-)
\ No newline at end of file
+}
+
+// Wait for the session file to appear
+waitForSessionFile(30);
diff --git a/src/main.ts b/src/main.ts
index 4d3fe54299..234d8d26c6 100644
--- a/src/main.ts
+++ b/src/main.ts
@@ -5,6 +5,7 @@
 'use strict';
 
 import vscode = require('vscode');
+import utils = require('./utils');
 import { Logger, LogLevel } from './logging';
 import { IFeature } from './feature';
 import { SessionManager } from './session';
@@ -28,6 +29,9 @@ var logger: Logger = undefined;
 var sessionManager: SessionManager = undefined;
 var extensionFeatures: IFeature[] = [];
 
+// Clean up the session file just in case one lingers from a previous session
+utils.deleteSessionFile();
+
 export function activate(context: vscode.ExtensionContext): void {
 
     vscode.languages.setLanguageConfiguration(
diff --git a/src/session.ts b/src/session.ts
index 8961e8cf00..4552954e96 100644
--- a/src/session.ts
+++ b/src/session.ts
@@ -257,11 +257,8 @@ export class SessionManager {
                     if (response["status"] === "started") {
                         let sessionDetails: utils.EditorServicesSessionDetails = response;
 
-                        // Write out the session configuration file
-                        utils.writeSessionFile(sessionDetails);
-
                         // Start the language service client
-                        this.startLanguageClient(sessionDetails.languageServicePort);
+                        this.startLanguageClient(sessionDetails);
                     }
                     else if (response["status"] === "failed") {
                         if (response["reason"] === "unsupported") {
@@ -326,12 +323,14 @@ export class SessionManager {
             .then((answer) => { if (answer === "Yes") { this.restartSession(); }});
     }
 
-    private startLanguageClient(port: number) {
+    private startLanguageClient(sessionDetails: utils.EditorServicesSessionDetails) {
 
-        this.log.write("Connecting to language service on port " + port + "..." + os.EOL);
+        var port = sessionDetails.languageServicePort;
 
         try
         {
+            this.log.write("Connecting to language service on port " + port + "..." + os.EOL);
+
             let connectFunc = () => {
                 return new Promise<StreamInfo>(
                     (resolve, reject) => {
@@ -339,6 +338,9 @@ export class SessionManager {
                         socket.on(
                             'connect',
                             () => {
+                                // Write out the session configuration file
+                                utils.writeSessionFile(sessionDetails);
+
                                 this.log.write("Language service connected.");
                                 resolve({writer: socket, reader: socket})
                             });