diff --git a/src/orchestrators/test.ts b/src/orchestrators/test.ts
index bbc5410..67d30a5 100644
--- a/src/orchestrators/test.ts
+++ b/src/orchestrators/test.ts
@@ -1,15 +1,19 @@
 
 import { OS, SpawnStatus } from 'codify-schemas';
 import os from 'node:os';
+import fs from 'node:fs'
+import path from 'node:path';
 
 import { PluginInitOrchestrator } from '../common/initialize-plugins.js';
-import { ProcessName, ctx, SubProcessName } from '../events/context.js';
+import { ProcessName, SubProcessName, ctx } from '../events/context.js';
 import { Reporter } from '../ui/reporters/reporter.js';
 import { StubReporter } from '../ui/reporters/stub-reporter.js';
+import { FileUtils } from '../utils/file.js';
 import { sleep } from '../utils/index.js';
 import { spawn, spawnSafe } from '../utils/spawn.js';
 import { PlanOrchestrator, PlanOrchestratorResponse } from './plan.js';
 import { ValidateOrchestrator } from './validate.js';
+import { OsUtils } from '../utils/os-utils.js';
 
 export interface TestArgs {
   path?: string;
@@ -20,13 +24,17 @@ export interface TestArgs {
 
 export const TestOrchestrator = {
   async run(args: TestArgs, reporter: Reporter): Promise<void> {
+    if (!OsUtils.isMacOS()) {
+      throw new Error('Only a MacOS host is supported currently for testing');
+    }
+
     ctx.processStarted(ProcessName.TEST);
     reporter.silent = true;
 
     ctx.subprocessStarted(SubProcessName.TEST_INITIALIZE_AND_VALIDATE);
     // Perform validation initially to ensure the project is valid
-    const initializationResult = await PluginInitOrchestrator.run({ ...args, noProgress: true }, new StubReporter());
-    await ValidateOrchestrator.run({ existing: initializationResult, noProgress: true }, new StubReporter());
+    const initializationResult = await PluginInitOrchestrator.run({ ...args, noProgress: true }, reporter);
+    await ValidateOrchestrator.run({ existing: initializationResult, noProgress: true }, reporter);
     ctx.subprocessFinished(SubProcessName.TEST_INITIALIZE_AND_VALIDATE);
 
     await this.ensureVmIsInstalled(reporter, args.vmOs);
@@ -36,8 +44,14 @@ export const TestOrchestrator = {
     const vmName = this.generateVmName();
     await spawnSafe(`tart clone ${baseVmName} ${vmName}`, { interactive: true });
 
+    // We want to install the latest Codify version which usually exists in ~/.local/share/codify/client/current unless it's not there.
+    const codifyInstall = (await FileUtils.dirExists('~/.local/share/codify/client/current'))
+      ? '~/.local/share/codify/client/current'
+      : '/usr/local/lib/codify';
+
     // Run this in the background. The user will have to manually exit the GUI to stop the test.
-    spawnSafe(`tart run ${vmName}`, { interactive: true })
+    // We bind mount the codify installation and the codify config directory. We choose not use :ro (read-only) because live changes are not supported in read-only mode.
+    spawnSafe(`tart run ${vmName} --dir=codify-lib:${codifyInstall}:ro --dir=codify-config:${path.dirname(initializationResult.project.codifyFiles[0])}:ro`, { interactive: true })
       .finally(() => {
         ctx.subprocessFinished(SubProcessName.TEST_USER_CONTINUE_ON_VM);
         ctx.subprocessStarted(SubProcessName.TEST_DELETING_VM);
@@ -49,7 +63,7 @@ export const TestOrchestrator = {
         console.log('VM has been killed... exiting.')
         process.exit(1);
       })
-    await sleep(10_000);
+    await sleep(5000);
     await this.waitUntilVmIsReady(vmName);
 
     ctx.subprocessFinished(SubProcessName.TEST_STARTING_VM);
@@ -58,12 +72,19 @@ export const TestOrchestrator = {
     // Install codify on the VM
     // await spawn(`tart exec ${vmName} /bin/bash -c "$(curl -fsSL https://releases.codifycli.com/install.sh)"`, { interactive: true });
     const { data: ip } = await spawnSafe(`tart ip ${vmName}`, { interactive: true });
-    await spawn(`sshpass -p "admin" scp -o PubkeyAuthentication=no -o StrictHostKeyChecking=no -o UserKnownHostsFile=/dev/null ${initializationResult.project.codifyFiles[0]} admin@${ip}:~/codify.jsonc`, { interactive: true });
 
-    if (args.vmOs === OS.Darwin) {
-      await spawn(`tart exec ${vmName} osascript -e "tell application \\"Terminal\\" to do script \\"cd ~/ && codify apply\\""`, { interactive: true });
-    } else {
-      await spawn(`tart exec ${vmName} gnome-terminal -- bash -c "cd ~/ && codify apply"`, { interactive: true });
+    try {
+      // Add symlinks to the bind mount locations.
+      await spawn(`tart exec ${vmName} sudo ln -s /Volumes/My\\ Shared\\ Files/codify-lib/bin/codify /usr/local/bin/codify`, { interactive: true });
+      await spawn(`tart exec ${vmName} ln -s /Volumes/My\\ Shared\\ Files/codify-config/${path.basename(initializationResult.project.codifyFiles[0])} /Users/admin/codify.jsonc`, { interactive: true });
+
+      // Launch terminal and run codify apply
+      await (args.vmOs === OS.Darwin ? spawn(`tart exec ${vmName} osascript -e "tell application \\"Terminal\\" to do script \\"cd ~ && codify apply\\""`, { interactive: true }) : spawn(`tart exec ${vmName} gnome-terminal -- bash -c "cd ~/ && codify apply"`, { interactive: true }));
+
+      this.watchAndSyncFileChanges(initializationResult.project.codifyFiles[0], ip);
+
+    } catch (error) {
+      ctx.log(`Error copying files to VM: ${error}`);
     }
 
     ctx.subprocessFinished(SubProcessName.TEST_COPYING_OVER_CONFIGS_AND_OPENING_TERMINAL);
@@ -136,5 +157,28 @@ export const TestOrchestrator = {
 
       await sleep(1000);
     }
+  },
+
+  watchAndSyncFileChanges(filePath: string, ip: string): void {
+    const watcher = fs.watch(filePath, { persistent: false }, async (eventType) => {
+      if (eventType === 'change') {
+        ctx.log('Config file changed, syncing to VM...');
+        try {
+          // Copy the updated config file to the VM
+          // This command will fail but it causes the bind mount to update for some reason. (seems like a bug in Tart). Leave this here for now.
+          await spawn(`sshpass -p "admin" scp -o PubkeyAuthentication=no -o StrictHostKeyChecking=no -o UserKnownHostsFile=/dev/null ${filePath} admin@${ip}:~/codify.jsonc`, { interactive: true });
+          // ctx.log('Config file synced successfully');
+        } catch (error) {
+          // ctx.log(`Error syncing config file: ${error}`);
+        }
+      }
+    });
+
+    // Clean up the watcher when the process finishes
+    const cleanupWatcher = () => {
+      watcher.close();
+    };
+
+    process.once('exit', cleanupWatcher);
   }
 };
diff --git a/src/ui/reporters/default-reporter.tsx b/src/ui/reporters/default-reporter.tsx
index 3ccb7e1..7073344 100644
--- a/src/ui/reporters/default-reporter.tsx
+++ b/src/ui/reporters/default-reporter.tsx
@@ -38,7 +38,7 @@ const ProgressLabelMapping = {
   [SubProcessName.TEST_INITIALIZE_AND_VALIDATE]: 'Initializing and validating your configs',
   [SubProcessName.TEST_CHECKING_VM_INSTALLED]: 'Checking if VM is installed',
   [SubProcessName.TEST_STARTING_VM]: 'Starting VM',
-  [SubProcessName.TEST_COPYING_OVER_CONFIGS_AND_OPENING_TERMINAL]: 'Copying over configs and opening terminal',
+  [SubProcessName.TEST_COPYING_OVER_CONFIGS_AND_OPENING_TERMINAL]: 'Copying over configs and opening terminal (if a confirmation dialog appears within the VM, please confirm it.)',
   [SubProcessName.TEST_USER_CONTINUE_ON_VM]: 'Done setup! Please continue on the VM UI',
   [SubProcessName.TEST_DELETING_VM]: 'Deleting VM',
 }
diff --git a/src/utils/file.ts b/src/utils/file.ts
index 1af7375..b622da8 100644
--- a/src/utils/file.ts
+++ b/src/utils/file.ts
@@ -22,6 +22,18 @@ export class FileUtils {
     }
   }
 
+  static async dirExists(dirPath: string, throwIfExistsButNotFile = true): Promise<boolean> {
+    try {
+      const result = await fs.lstat(path.resolve(dirPath))
+      if (throwIfExistsButNotFile && !result.isDirectory()) {
+        throw new Error(`File found at ${dirPath} instead of a file`)
+      }
+      return true;
+    } catch(e) {
+      return false;
+    }
+  }
+
   static async isDir(fileOrDir: string): Promise<boolean> {
     const lstat = await fs.lstat(path.resolve(fileOrDir))
     return lstat.isDirectory()
diff --git a/src/utils/spawn.ts b/src/utils/spawn.ts
index 4f4bd9d..288154d 100644
--- a/src/utils/spawn.ts
+++ b/src/utils/spawn.ts
@@ -65,14 +65,7 @@ export async function spawnSafe(cmd: string, options?: SpawnOptions, pluginName?
     const initialCols = process.stdout.columns ?? 80;
     const initialRows = process.stdout.rows ?? 24;
 
-    // Mac OS uses -SN instead of -Sn
-    let command;
-    if (OsUtils.isMacOS()) {
-      command = options?.requiresRoot ? `sudo -k >/dev/null 2>&1; sudo -SN <<< "${password}" -E ${ShellUtils.getDefaultShell()} ${options?.interactive ? '-i' : ''} -c "${cmd.replaceAll('\'', '\\\'')}"` : cmd;
-    } else {
-      command = options?.requiresRoot ? `sudo -k >/dev/null 2>&1; sudo -S <<< "${password}" -E ${ShellUtils.getDefaultShell()} ${options?.interactive ? '-i' : ''} -c '${cmd.replaceAll('\'', '\\\'')}'` : cmd;
-    }
-
+    const command = options?.requiresRoot ? `sudo -k >/dev/null 2>&1; sudo -S <<< "${password}" -E ${ShellUtils.getDefaultShell()} ${options?.interactive ? '-i' : ''} -c "${cmd.replaceAll('"', '\\"')}"` : cmd;
     const args = options?.interactive ? ['-i', '-c', command] : ['-c', command]
 
     // Run the command in a pty for interactivity