diff --git a/src/interactive-window/debugger/jupyter/kernelDebugAdapter.ts b/src/interactive-window/debugger/jupyter/kernelDebugAdapter.ts
index a1c8065d07a..f7473d6f067 100644
--- a/src/interactive-window/debugger/jupyter/kernelDebugAdapter.ts
+++ b/src/interactive-window/debugger/jupyter/kernelDebugAdapter.ts
@@ -9,7 +9,7 @@ import { DebugAdapterTracker, DebugSession, NotebookDocument, Uri } from 'vscode
 import { DebugProtocol } from 'vscode-debugprotocol';
 import { IKernel, IKernelConnectionSession } from '../../../kernels/types';
 import { IPlatformService } from '../../../platform/common/platform/types';
-import { IDumpCellResponse, IDebugLocationTrackerFactory } from '../../../notebooks/debugger/debuggingTypes';
+import { IDebugLocationTrackerFactory } from '../../../notebooks/debugger/debuggingTypes';
 import { traceError, traceInfo, traceInfoIfCI } from '../../../platform/logging';
 import { getInteractiveCellMetadata } from '../../../interactive-window/helpers';
 import { KernelDebugAdapterBase } from '../../../notebooks/debugger/kernelDebugAdapterBase';
@@ -90,7 +90,8 @@ export class KernelDebugAdapter extends KernelDebugAdapterBase {
             const response = await this.session.customRequest('dumpCell', { code });
 
             // We know jupyter will strip out leading white spaces, hence take that into account.
-            const norm = path.normalize((response as IDumpCellResponse).sourcePath);
+            const norm = KernelDebugAdapterBase.normalizeFsAware(response.sourcePath);
+            traceInfoIfCI(`KernelDebugAdapter::dumpCell ${response.sourcePath} -> ${norm}`);
             this.fileToCell.set(norm, Uri.parse(metadata.interactive.uristring));
 
             // If this cell doesn't have a cell marker, then
diff --git a/src/notebooks/debugger/kernelDebugAdapter.ts b/src/notebooks/debugger/kernelDebugAdapter.ts
index c6ee1bd5bda..3e42ba62e47 100644
--- a/src/notebooks/debugger/kernelDebugAdapter.ts
+++ b/src/notebooks/debugger/kernelDebugAdapter.ts
@@ -3,11 +3,10 @@
 
 'use strict';
 
-import * as path from '../../platform/vscode-path/path';
-import { IDumpCellResponse } from './debuggingTypes';
-import { traceError } from '../../platform/logging';
+import { traceError, traceInfoIfCI } from '../../platform/logging';
 import { KernelDebugAdapterBase } from './kernelDebugAdapterBase';
 import { DebugProtocol } from 'vscode-debugprotocol';
+import { IDumpCellResponse } from './debuggingTypes';
 
 /**
  * Concrete implementation of the KernelDebugAdapterBase class that will dump cells
@@ -19,10 +18,11 @@ export class KernelDebugAdapter extends KernelDebugAdapterBase {
     protected override async dumpCell(index: number): Promise<void> {
         const cell = this.notebookDocument.cellAt(index);
         try {
-            const response = await this.session.customRequest('dumpCell', {
+            const response = (await this.session.customRequest('dumpCell', {
                 code: cell.document.getText().replace(/\r\n/g, '\n')
-            });
-            const norm = path.normalize((response as IDumpCellResponse).sourcePath);
+            })) as IDumpCellResponse;
+            const norm = KernelDebugAdapterBase.normalizeFsAware(response.sourcePath);
+            traceInfoIfCI(`KernelDebugAdapter::dumpCell ${response.sourcePath} -> ${norm}`);
             this.fileToCell.set(norm, cell.document.uri);
             this.cellToFile.set(cell.document.uri.toString(), norm);
         } catch (err) {
diff --git a/src/notebooks/debugger/kernelDebugAdapterBase.ts b/src/notebooks/debugger/kernelDebugAdapterBase.ts
index 5d2dba511a9..2a0943afe3e 100644
--- a/src/notebooks/debugger/kernelDebugAdapterBase.ts
+++ b/src/notebooks/debugger/kernelDebugAdapterBase.ts
@@ -264,6 +264,23 @@ export abstract class KernelDebugAdapterBase implements DebugAdapter, IKernelDeb
         });
     }
 
+    static normalizeFsAware(sourcePath: string) {
+        // If the kernel runs on Windows, then do windows-style path normalization
+        // (see https://github.com/ipython/ipykernel/issues/995).
+        let norm = '';
+        if (sourcePath.match(/^[A-Za-z]:/)) {
+            norm = path.win32.normalize(sourcePath);
+        } else {
+            traceInfoIfCI(
+                `KernelDebugAdapter::normalizeFsAware ${sourcePath} would normalize to ${path.posix.normalize(
+                    sourcePath
+                )}`
+            );
+            norm = path.posix.normalize(sourcePath);
+        }
+        return norm;
+    }
+
     private lookupCellByLongName(sourcePath: string) {
         if (!this.platformService.isWindows) {
             return undefined;