diff --git a/core/llm/llms/AiderLLM.ts b/core/llm/llms/AiderLLM.ts
index 720c489a16..e3a53ba8dd 100644
--- a/core/llm/llms/AiderLLM.ts
+++ b/core/llm/llms/AiderLLM.ts
@@ -158,6 +158,7 @@ class Aider extends BaseLLM {
     let responseComplete = false;
     let potentialCompletion = false;
     let potentialCompletionTimeout: NodeJS.Timeout | null = null;
+    let startedListening = false;
 
     const escapeDollarSigns = (text: string | undefined) => {
       if (!text) {
@@ -182,6 +183,7 @@ class Aider extends BaseLLM {
           potentialCompletion = false;
         }
 
+
         if (READY_PROMPT_REGEX.test(newOutput)) {
           // Instead of marking complete immediately, set up potential completion
           if (!potentialCompletion) {
@@ -193,10 +195,18 @@ class Aider extends BaseLLM {
         }
 
         lastProcessedIndex = Aider.aiderProcess?.aiderOutput.length || 0;
-        yield {
-          role: "assistant",
-          content: escapeDollarSigns(newOutput),
-        };
+        
+        // Start listening once we see a newline-prefixed message
+        if (!startedListening && newOutput.startsWith('\n')) {
+          startedListening = true;
+        }
+
+        if (startedListening) {
+          yield {
+            role: "assistant",
+            content: escapeDollarSigns(newOutput),
+          };
+        }
 
         if (Aider.aiderProcess?.state.state === "stopped" || Aider.aiderProcess?.state.state === "crashed") {
           if (potentialCompletionTimeout) {
diff --git a/extensions/vscode/src/integrations/aider/aiderProcess.ts b/extensions/vscode/src/integrations/aider/aiderProcess.ts
index 127ad51b42..d21552f3cc 100644
--- a/extensions/vscode/src/integrations/aider/aiderProcess.ts
+++ b/extensions/vscode/src/integrations/aider/aiderProcess.ts
@@ -29,18 +29,62 @@ export const AIDER_QUESTION_MARKER = "[Yes]\\:";
 export const AIDER_END_MARKER = "─────────────────────────────────────";
 export const COMPLETION_DELAY = 1500; // 1.5 seconds wait time
 
-function updateAiderVersion() {
+async function updateAiderVersion() {
   try {
-    if (compareVersions(getAiderVersion(), PEARAI_AIDER_VERSION) != 0) {
-      console.log(`Upgrading aider-chat to version: ${PEARAI_AIDER_VERSION}`); 
-      execSync(`pipx uninstall aider-chat`); 
-      execSync(`pipx install aider-chat==${PEARAI_AIDER_VERSION}`);
+    const aiderVersion = getAiderVersion();
+    console.log(`Current aider version: ${aiderVersion}`);
+    
+    if (compareVersions(aiderVersion, PEARAI_AIDER_VERSION) === 0) {
+      return; // Already on correct version
     }
+
+    console.log(`Upgrading aider-chat to version: ${PEARAI_AIDER_VERSION}`);
+    await updateUsingPackageManager();
   } catch (error) {
     console.error("Error updating Aider version:", error);
   }
 }
 
+async function updateUsingPackageManager() {
+  const updateMethods = [
+    {
+      name: 'pipx reinstall',
+      command: async () => {
+        await execSync(`pipx uninstall aider-chat`);
+        await execSync(`pipx install aider-chat==${PEARAI_AIDER_VERSION}`);
+      }
+    },
+    {
+      name: 'pipx upgrade',
+      command: async () => await execSync(`pipx upgrade aider-chat`)
+    },
+    {
+      name: 'brew upgrade',
+      condition: () => IS_MAC || IS_LINUX,
+      command: async () => await execSync(`brew upgrade aider`)
+    }
+  ];
+
+  for (const method of updateMethods) {
+    if (method.condition && !method.condition()) {
+      continue;
+    }
+
+    try {
+      await method.command();
+      console.log(`Successfully updated using ${method.name}`);
+      vscode.commands.executeCommand("pearai.aiderResetSession");
+      return;
+    } catch (error) {
+      console.log(`${method.name} failed:`, error);
+      // Continue to next method
+    }
+  }
+
+  throw new Error('All update methods failed');
+}
+
+
 function getAiderVersion(): string {
   try {
     const versionOutput = execSync('aider --version').toString().trim();
@@ -78,7 +122,7 @@ export function buildAiderCommand(model: string, accessToken: string | undefined
     "--map-tokens", "2048",
     "--subtree-only",
     "--no-show-release-notes",
-    // "--no-detect-urls" // TODO: Add with aider update
+    "--no-detect-urls"
   ];
 
 
@@ -335,6 +379,12 @@ async startAiderChat(model: string, apiKey: string | undefined, isRestarting: bo
         }
       });
     }
+    
+    if (this.aiderProcess.stderr) {
+      this.aiderProcess.stderr.on('data', (data: Buffer) => {
+        console.error('Aider process stderr:', data.toString());
+      });
+    }
 
     this.aiderProcess.on('exit', (code, signal) => {
       console.log(`Aider process exited with code ${code}, signal ${signal}`);
diff --git a/extensions/vscode/src/integrations/aider/aiderUtil.ts b/extensions/vscode/src/integrations/aider/aiderUtil.ts
index e2dcef1d48..bfa2ae52cb 100644
--- a/extensions/vscode/src/integrations/aider/aiderUtil.ts
+++ b/extensions/vscode/src/integrations/aider/aiderUtil.ts
@@ -9,7 +9,7 @@ import { isFirstPearAICreatorLaunch } from "../../copySettings";
 import { VsCodeWebviewProtocol } from "../../webviewProtocol";
 import * as os from "os";
 
-export const PEARAI_AIDER_VERSION = "0.64.0";
+export const PEARAI_AIDER_VERSION = "0.65.0";
 
 const PLATFORM = process.platform;
 const IS_WINDOWS = PLATFORM === "win32";
@@ -149,26 +149,53 @@ export async function installAider(core: Core) {
 
     vscode.window.showInformationMessage("Installing Aider...");
 
-    let command = "";
+    let success = false;
+    
     if (IS_WINDOWS) {
-      command += "python -m pip install pipx;";
-      command += "pipx ensurepath;";
-      command += `pipx install aider-chat==${PEARAI_AIDER_VERSION};`;
-      command += `echo "\nAider ${PEARAI_AIDER_VERSION} installation complete."`;
+      const command = [
+        "python -m pip install pipx",
+        "pipx ensurepath",
+        `pipx install aider-chat==${PEARAI_AIDER_VERSION}`,
+        `echo "\nAider ${PEARAI_AIDER_VERSION} installation complete."`
+      ].join(";");
+
+      try {
+        execSync(command);
+        success = true;
+      } catch (error) {
+        console.error("Failed to install Aider via pipx on Windows:", error);
+        return true;
+      }
     } else {
-      command += "brew install pipx;";
-      command += `pipx install aider-chat==${PEARAI_AIDER_VERSION};`;
-      command += `echo "\nAider ${PEARAI_AIDER_VERSION} installation complete."`;
+      // For Mac/Linux, try pipx first
+      try {
+        const pipxCommand = [
+          "brew install pipx",
+          `pipx install aider-chat==${PEARAI_AIDER_VERSION}`,
+          `echo "\nAider ${PEARAI_AIDER_VERSION} installation complete."`
+        ].join(";");
+        
+        execSync(pipxCommand);
+        success = true;
+      } catch (pipxError) {
+        console.log("Failed to install Aider via pipx, trying brew...");
+        
+        // If pipx fails, try installing directly with brew
+        try {
+          execSync("brew install aider");
+          success = true;
+        } catch (brewError) {
+          console.error("Failed to install Aider via brew:", brewError);
+          return true;
+        }
+      }
     }
 
-    try {
-      execSync(command);
+    if (success) {
       core.invoke("llm/startAiderProcess", undefined);
       return false;
-    } catch (error) {
-      console.error("Failed to execute Aider command:", error);
-      return true;
     }
+    return true;
   }
 }