diff --git a/extension/debug/debug.ts b/extension/debug/debug.ts
index 95bd7f6..9e02146 100644
--- a/extension/debug/debug.ts
+++ b/extension/debug/debug.ts
@@ -126,12 +126,15 @@ class MojoDebugAdapterDescriptorFactory
     }
     this.logger.info(`Using the SDK ${sdk.version} for the debug session`);
 
-    return new vscode.DebugAdapterExecutable(sdk.dapPath, [
-      '--repl-mode',
-      'variable',
-      '--pre-init-command',
-      `?!plugin load '${sdk.lldbPluginPath}'`,
-    ]);
+    this.logger.debug('env', sdk.getProcessEnv());
+
+    return new vscode.DebugAdapterExecutable(
+      sdk.dapPath,
+      ['--repl-mode', 'variable'],
+      {
+        env: sdk.getProcessEnv(),
+      },
+    );
   }
 }
 
@@ -264,6 +267,7 @@ class MojoDebugConfigurationResolver
 
     // This setting shortens the length of address strings.
     const initCommands = [
+      `?!plugin load '${sdk.lldbPluginPath}'`,
       '?settings set target.show-hex-variable-values-with-leading-zeroes false',
       // FIXME(#23274): remove this when we properly emit the opt flag.
       '?settings set target.process.optimization-warnings false',
diff --git a/extension/pyenv.ts b/extension/pyenv.ts
index 5f8ffb2..8690826 100644
--- a/extension/pyenv.ts
+++ b/extension/pyenv.ts
@@ -115,6 +115,7 @@ class HomeSDK extends SDK {
     mojoPath: string,
     visualizersPath: string,
     lldbPath: string,
+    private prefixPath?: string,
   ) {
     super(
       logger,
@@ -132,8 +133,10 @@ class HomeSDK extends SDK {
 
   public override getProcessEnv(withTelemetry: boolean = true) {
     return {
+      ...super.getProcessEnv(withTelemetry),
       MODULAR_HOME: this.homePath,
-      MODULAR_TELEMETRY_ENABLED: withTelemetry ? 'true' : 'false',
+      // HACK: Set CONDA_PREFIX to allow debugger wrappers to work
+      CONDA_PREFIX: this.prefixPath,
     };
   }
 }
@@ -214,6 +217,7 @@ export class PythonEnvironmentManager extends DisposableContext {
       return this.createSDKFromHomePath(
         SDKKind.Environment,
         path.join(env.executable.sysPrefix, 'share', 'max'),
+        env.executable.sysPrefix,
       );
     } else {
       this.logger.info(
@@ -315,6 +319,7 @@ export class PythonEnvironmentManager extends DisposableContext {
   public async createSDKFromHomePath(
     kind: SDKKind,
     homePath: string,
+    prefixPath?: string,
   ): Promise<SDK | undefined> {
     const modularCfgPath = path.join(homePath, 'modular.cfg');
     const decoder = new TextDecoder();
@@ -372,6 +377,7 @@ export class PythonEnvironmentManager extends DisposableContext {
         config['mojo-max']['driver_path'],
         config['mojo-max']['lldb_visualizers_path'],
         config['mojo-max']['lldb_path'],
+        prefixPath,
       );
     } catch (e) {
       await this.displaySDKError(