diff --git a/js/VSC-Extension/packages/sidebar-webview/src/components/initForm.tsx b/js/VSC-Extension/packages/sidebar-webview/src/components/initForm.tsx
index e68160624..bfb08ee8e 100644
--- a/js/VSC-Extension/packages/sidebar-webview/src/components/initForm.tsx
+++ b/js/VSC-Extension/packages/sidebar-webview/src/components/initForm.tsx
@@ -63,6 +63,13 @@ const InitForm = ({ suggestions, errorDetails, pyprojectPath }: Props) => {
   });
   const renderedOnPurpose = !errorDetails;
 
+  // Helper to get directory name from path
+  const getConfigDirectory = () => {
+    if (!pyprojectPath) return "workspace root";
+    const parts = pyprojectPath.split("/");
+    return parts.length > 1 ? parts.slice(0, -1).join("/") : ".";
+  };
+
   const setActiveTab = renderedOnPurpose
     ? useStore((state) => state.setActiveTab)
     : undefined;
@@ -315,6 +322,20 @@ const InitForm = ({ suggestions, errorDetails, pyprojectPath }: Props) => {
         className={styles.form}
       >
         <h2 className={styles.title}>Project Configuration</h2>
+
+        {/* Context info section */}
+        <div className={styles.contextInfo}>
+          <div className={styles.contextItem}>
+            <span className="codicon codicon-file"></span>
+            <span>
+              Config file: <code>{pyprojectPath || "pyproject.toml (will be created)"}</code>
+            </span>
+          </div>
+          <div className={styles.helpText}>
+            💡 All paths below are relative to <code>{getConfigDirectory()}</code>
+          </div>
+        </div>
+
         {errorDetails && (
           <p
             className={styles.bannerError}
@@ -332,13 +353,15 @@ style="color: var(--vscode-editorWarning-foreground);"></span>` + errorDetails,
           "Module Root",
           "Path relative to pyproject.toml where your source code is located.",
           true,
+          "e.g., src, lib, app, or . for current directory"
         )}
 
         {renderField(
           "tests_root",
           "Tests Root",
-          "Path relative to pyproject.toml where your test files are located",
+          "Path relative to pyproject.toml where your test files are located (common: tests, test, __tests__)",
           true,
+          "e.g., tests, test, or . for current directory"
         )}
 
         {renderField(
@@ -374,12 +397,23 @@ style="color: var(--vscode-editorWarning-foreground);"></span>` + errorDetails,
             disabled={isLoading}
           >
             {isLoading ? (
-              <span className="codicon codicon-loading spin"></span>
+              <>
+                <span className="codicon codicon-loading spin"></span>
+                {" Saving..."}
+              </>
             ) : (
-              "Save Configurations"
+              <>
+                <span className="codicon codicon-save"></span>
+                {" Save & Apply Configuration"}
+              </>
             )}
           </button>
         </div>
+        {!isLoading && (
+          <div className={styles.actionHelp}>
+            {pyprojectPath ? "This will update" : "This will create"} your pyproject.toml and reload the extension
+          </div>
+        )}
       </form>
     </div>
   );
diff --git a/js/VSC-Extension/packages/sidebar-webview/src/styles/initForm.module.css b/js/VSC-Extension/packages/sidebar-webview/src/styles/initForm.module.css
index ab33a0caa..6325911b9 100644
--- a/js/VSC-Extension/packages/sidebar-webview/src/styles/initForm.module.css
+++ b/js/VSC-Extension/packages/sidebar-webview/src/styles/initForm.module.css
@@ -33,6 +33,57 @@
   color: var(--vscode-foreground);
 }
 
+.contextInfo {
+  background: var(--vscode-input-background);
+  border: 1px solid var(--vscode-input-border);
+  border-radius: 4px;
+  padding: 12px;
+  margin: 8px 0 16px 0;
+  display: flex;
+  flex-direction: column;
+  gap: 8px;
+}
+
+.contextItem {
+  display: flex;
+  align-items: center;
+  gap: 8px;
+  font-size: 12px;
+  color: var(--vscode-descriptionForeground);
+}
+
+.contextItem code {
+  background: var(--vscode-textCodeBlock-background);
+  padding: 2px 6px;
+  border-radius: 3px;
+  font-family: var(--vscode-editor-font-family);
+  font-size: 11px;
+  color: var(--vscode-textPreformat-foreground);
+}
+
+.helpText {
+  font-size: 11px;
+  color: var(--vscode-descriptionForeground);
+  font-style: italic;
+  margin-top: 4px;
+}
+
+.helpText code {
+  background: var(--vscode-textCodeBlock-background);
+  padding: 2px 4px;
+  border-radius: 3px;
+  font-family: var(--vscode-editor-font-family);
+  font-size: 10px;
+}
+
+.actionHelp {
+  font-size: 11px;
+  color: var(--vscode-descriptionForeground);
+  text-align: center;
+  margin-top: 4px;
+  font-style: italic;
+}
+
 .bannerError {
   padding: 1rem 0.5rem;
   border-radius: 5px;
diff --git a/js/VSC-Extension/src/boot/bootCodeflashServer.ts b/js/VSC-Extension/src/boot/bootCodeflashServer.ts
index bdba6c9d0..c91f111c1 100644
--- a/js/VSC-Extension/src/boot/bootCodeflashServer.ts
+++ b/js/VSC-Extension/src/boot/bootCodeflashServer.ts
@@ -177,17 +177,38 @@ export class BootCodeflashServerStep extends BaseStep {
     };
   };
 
+  /**When
+   * Safely register a VS Code command with error handling.
+   * If a command already exists (e.g., during extension reload), log a warning
+   * and return a no-op disposable to prevent crashes.
+   */
+  private safeRegisterCommand = (
+    commandId: string,
+    callback: (...args: any[]) => any,
+  ): vscode.Disposable => {
+    try {
+      return vscode.commands.registerCommand(commandId, callback);
+    } catch (error) {
+      // Command already exists - this can happen during extension reload/retry
+      this.logger.warn(
+        `Command '${commandId}' already registered. This is expected during extension reload. Error: ${error}`,
+      );
+      // Return a no-op disposable to maintain the disposal chain
+      return { dispose: () => {} };
+    }
+  };
+
   private provideCommands = (
     sidebarProvider: SidebarProvider,
     commentThreadProvider: CommentThreadProvider,
   ) => {
-    const optimizeFunctionCommand = vscode.commands.registerCommand(
+    const optimizeFunctionCommand = this.safeRegisterCommand(
       "codeflash.optimizeFunction",
       (uri: vscode.Uri, functionName: string) => {
         sidebarProvider.addFunctionToQueue(functionName, uri, true);
       },
     );
-    const clearAllTasksCommand = vscode.commands.registerCommand(
+    const clearAllTasksCommand = this.safeRegisterCommand(
       "codeflash.clearAllTasks",
       () => {
         const allTasksIds = this.globalState
@@ -199,7 +220,7 @@ export class BootCodeflashServerStep extends BaseStep {
         commentThreadProvider.scheduleRefresh();
       },
     );
-    const optimizeAllCommand = vscode.commands.registerCommand(
+    const optimizeAllCommand = this.safeRegisterCommand(
       "codeflash.optimizeAll",
       async () => {
         this.logger.info("Optimizing all functions from command");
@@ -207,7 +228,7 @@ export class BootCodeflashServerStep extends BaseStep {
       },
     );
 
-    const viewOptimization = vscode.commands.registerCommand(
+    const viewOptimization = this.safeRegisterCommand(
       "codeflash.viewPatch",
       async (
         threadOrPayload:
@@ -229,7 +250,7 @@ export class BootCodeflashServerStep extends BaseStep {
       },
     );
 
-    const acceptInlineCommentOptimizationCmd = vscode.commands.registerCommand(
+    const acceptInlineCommentOptimizationCmd = this.safeRegisterCommand(
       "codeflash.acceptInlineRefactor",
       async (
         thread: vscode.CommentThread & {
@@ -242,7 +263,7 @@ export class BootCodeflashServerStep extends BaseStep {
       },
     );
 
-    const sendMessage = vscode.commands.registerCommand(
+    const sendMessage = this.safeRegisterCommand(
       "codeflash.sendMessage",
       (message: OutgoingWebviewMessage) => {
         sidebarProvider.sendMessage(message);
diff --git a/js/VSC-Extension/src/services/initService.ts b/js/VSC-Extension/src/services/initService.ts
index 1d63256ba..d5f756da8 100644
--- a/js/VSC-Extension/src/services/initService.ts
+++ b/js/VSC-Extension/src/services/initService.ts
@@ -109,13 +109,22 @@ export class InitService extends Disposable {
     } catch (error) {
       if (maxRetries > 0) {
         this.logger.error(
-          `InitService init error: ${error} (${maxRetries} retries left`,
+          `InitService init error: ${error} (${maxRetries} retries left)`,
         );
 
+        // Dispose all resources including LSP clients and command registrations
         this.dispose();
         this._disposables = [];
-        // wait for half a second before retrying
-        await new Promise((resolve) => setTimeout(resolve, 500));
+
+        // Wait longer (1 second) to ensure VS Code fully unregisters commands and disposes resources
+        // This prevents "command already exists" errors during retry
+        // The delay accounts for:
+        // 1. Async disposal of LSP clients
+        // 2. VS Code's internal command registry cleanup
+        // 3. Event listener teardown
+        this.logger.info("Waiting for cleanup to complete before retry...");
+        await new Promise((resolve) => setTimeout(resolve, 1000));
+
         return await this.initWithRetries(maxRetries - 1);
       } else {
         this.logger.error(`InitService init failed: ${error}`);
diff --git a/lefthook.yml b/lefthook.yml
index 843c21f88..94ae12562 100644
--- a/lefthook.yml
+++ b/lefthook.yml
@@ -2,10 +2,9 @@ pre-commit:
   parallel: true
   commands:
     secret-scan:
-      runner: "node"
       glob: "*"
       exclude: "node_modules/**|venv/**|.venv/**|__pycache__/**|dist/**|build/**"
-      command: "./node_modules/.bin/secretlint {staged_files} --maskSecrets --config ./secretlint.config.js"
+      run: "./node_modules/.bin/secretlint {staged_files} --maskSecrets --secretlintrc ./secretlint.config.js"
 
 #    js-lint:
 #      runner: "node"