diff --git a/src/client/pythonEnvironments/base/locators/lowLevel/fsWatchingLocator.ts b/src/client/pythonEnvironments/base/locators/lowLevel/fsWatchingLocator.ts
index fab78d42de05..7181ec975eea 100644
--- a/src/client/pythonEnvironments/base/locators/lowLevel/fsWatchingLocator.ts
+++ b/src/client/pythonEnvironments/base/locators/lowLevel/fsWatchingLocator.ts
@@ -143,6 +143,7 @@ export abstract class FSWatchingLocator<I = PythonEnvInfo> extends LazyResourceB
             const searchLocation = Uri.file(
                 this.opts.searchLocation ?? path.dirname(getEnvironmentDirFromPath(executable)),
             );
+            traceVerbose('Fired event ', JSON.stringify({ type, kind, searchLocation }), 'from locator');
             this.emitter.fire({ type, kind, searchLocation });
         };
 
diff --git a/src/client/pythonEnvironments/common/externalDependencies.ts b/src/client/pythonEnvironments/common/externalDependencies.ts
index 27f5cea2ee4d..058f0fb59d15 100644
--- a/src/client/pythonEnvironments/common/externalDependencies.ts
+++ b/src/client/pythonEnvironments/common/externalDependencies.ts
@@ -85,6 +85,9 @@ export function isParentPath(filePath: string, parentPath: string): boolean {
     if (!parentPath.endsWith(path.sep)) {
         parentPath += path.sep;
     }
+    if (!filePath.endsWith(path.sep)) {
+        filePath += path.sep;
+    }
     return normCasePath(filePath).startsWith(normCasePath(parentPath));
 }
 
diff --git a/src/client/pythonEnvironments/common/pythonBinariesWatcher.ts b/src/client/pythonEnvironments/common/pythonBinariesWatcher.ts
index 364157b02fb0..3cdf9860814b 100644
--- a/src/client/pythonEnvironments/common/pythonBinariesWatcher.ts
+++ b/src/client/pythonEnvironments/common/pythonBinariesWatcher.ts
@@ -27,7 +27,7 @@ export function watchLocationForPythonBinaries(
     const resolvedGlob = path.posix.normalize(executableGlob);
     const [baseGlob] = resolvedGlob.split('/').slice(-1);
     function callbackClosure(type: FileChangeType, e: string) {
-        traceVerbose('Received event', JSON.stringify(e), 'for baseglob', baseGlob);
+        traceVerbose('Received event', type, JSON.stringify(e), 'for baseglob', baseGlob);
         const isMatch = minimatch(path.basename(e), baseGlob, { nocase: getOSType() === OSType.Windows });
         if (!isMatch) {
             // When deleting the file for some reason path to all directories leading up to python are reported
diff --git a/src/client/pythonEnvironments/legacyIOC.ts b/src/client/pythonEnvironments/legacyIOC.ts
index 25ea840d8976..0b18fb2c11e3 100644
--- a/src/client/pythonEnvironments/legacyIOC.ts
+++ b/src/client/pythonEnvironments/legacyIOC.ts
@@ -5,7 +5,7 @@ import { injectable } from 'inversify';
 import { intersection } from 'lodash';
 import * as vscode from 'vscode';
 import { DiscoveryVariants } from '../common/experiments/groups';
-import { traceError } from '../common/logger';
+import { traceError, traceVerbose } from '../common/logger';
 import { FileChangeType } from '../common/platform/fileSystemWatcher';
 import { Resource } from '../common/types';
 import {
@@ -177,6 +177,7 @@ class ComponentAdapter implements IComponentAdapter {
             if (!workspaceFolder || !e.searchLocation) {
                 return;
             }
+            traceVerbose(`Recieved event ${JSON.stringify(e)} file change event`);
             if (
                 e.type === FileChangeType.Created &&
                 isParentPath(e.searchLocation.fsPath, workspaceFolder.uri.fsPath)