diff --git a/packages/backend-plugin-manager/src/manager/plugin-manager.test.ts b/packages/backend-plugin-manager/src/manager/plugin-manager.test.ts
index 8a17fe082a..d7433da2d6 100644
--- a/packages/backend-plugin-manager/src/manager/plugin-manager.test.ts
+++ b/packages/backend-plugin-manager/src/manager/plugin-manager.test.ts
@@ -174,20 +174,23 @@ describe('backend-plugin-manager', () => {
                 meta: {
                   name: 'Error',
                   message: expect.stringContaining(
-                    `Cannot find module '${url.fileURLToPath(
-                      location,
-                    )}/dist/index.cjs.js' from `,
+                    `Cannot find module '${path.resolve(
+                      url.fileURLToPath(location),
+                      'dist/index.cjs.js',
+                    )}' from `,
                   ),
                   _originalMessage: expect.stringContaining(
-                    `Cannot find module '${url.fileURLToPath(
-                      location,
-                    )}/dist/index.cjs.js' from `,
+                    `Cannot find module '${path.resolve(
+                      url.fileURLToPath(location),
+                      'dist/index.cjs.js',
+                    )}' from `,
                   ),
                   code: 'MODULE_NOT_FOUND',
                   hint: '',
-                  moduleName: `${url.fileURLToPath(
-                    location,
-                  )}/dist/index.cjs.js`,
+                  moduleName: `${path.resolve(
+                    url.fileURLToPath(location),
+                    'dist/index.cjs.js',
+                  )}`,
                   siblingWithSimilarExtensionFound: false,
                   requireStack: undefined,
                 },
@@ -351,7 +354,9 @@ describe('backend-plugin-manager', () => {
       },
     ])('$name', async (tc: TestCase): Promise<void> => {
       const plugin: ScannedPluginPackage = {
-        location: new URL(`file:///node_modules/jest-tests/${randomUUID()}`),
+        location: url.pathToFileURL(
+          path.resolve(`/node_modules/jest-tests/${randomUUID()}`),
+        ),
         manifest: tc.packageManifest,
       };
 
@@ -462,8 +467,8 @@ describe('backend-plugin-manager', () => {
         .spyOn(PluginScanner.prototype, 'scanRoot')
         .mockImplementation(async () => [
           {
-            location: new URL(
-              'file:///somewhere/dynamic-plugins-root/a-dynamic-plugin',
+            location: url.pathToFileURL(
+              path.resolve('/somewhere/dynamic-plugins-root/a-dynamic-plugin'),
             ),
             manifest: {
               name: 'test',
@@ -528,10 +533,12 @@ describe('backend-plugin-manager', () => {
       expect(scanRootSpier).toHaveBeenCalled();
       expect(mockedModuleLoader.bootstrap).toHaveBeenCalledWith(
         findPaths(__dirname).targetRoot,
-        ['/somewhere-else/a-dynamic-plugin'],
+        [path.resolve('/somewhere-else/a-dynamic-plugin')],
       );
       expect(mockedModuleLoader.load).toHaveBeenCalledWith(
-        '/somewhere/dynamic-plugins-root/a-dynamic-plugin/dist/index.cjs.js',
+        path.resolve(
+          '/somewhere/dynamic-plugins-root/a-dynamic-plugin/dist/index.cjs.js',
+        ),
       );
     });
   });
diff --git a/packages/backend-plugin-manager/src/scanner/plugin-scanner-watcher.test.ts b/packages/backend-plugin-manager/src/scanner/plugin-scanner-watcher.test.ts
index 5ced3cfbab..e346bf749f 100644
--- a/packages/backend-plugin-manager/src/scanner/plugin-scanner-watcher.test.ts
+++ b/packages/backend-plugin-manager/src/scanner/plugin-scanner-watcher.test.ts
@@ -15,7 +15,7 @@
  */
 
 import { PluginScanner } from './plugin-scanner';
-import { Logs, MockedLogger } from '../__testUtils__/testUtils';
+import { LogContent, Logs, MockedLogger } from '../__testUtils__/testUtils';
 import { Config, ConfigReader } from '@backstage/config';
 import path, { join } from 'path';
 import { ScannedPluginPackage } from './types';
@@ -126,10 +126,16 @@ describe('plugin-scanner', () => {
       expect(logger.logs).toEqual<Logs>({
         infos: [
           {
-            message: `rootDirectory changed (addDir - ${backstageRootDirectory}/first-dir/test-backend-plugin): scanning plugins again`,
+            message: `rootDirectory changed (addDir - ${path.resolve(
+              backstageRootDirectory,
+              'first-dir/test-backend-plugin',
+            )}): scanning plugins again`,
           },
           {
-            message: `rootDirectory changed (add - ${backstageRootDirectory}/first-dir/test-backend-plugin/package.json): scanning plugins again`,
+            message: `rootDirectory changed (add - ${path.resolve(
+              backstageRootDirectory,
+              'first-dir/test-backend-plugin/package.json',
+            )}): scanning plugins again`,
           },
         ],
       });
@@ -151,7 +157,10 @@ describe('plugin-scanner', () => {
       expect(logger.logs).toEqual<Logs>({
         infos: [
           {
-            message: `rootDirectory changed in Config from '${backstageRootDirectory}/first-dir' to '${backstageRootDirectory}/second-dir'`,
+            message: `rootDirectory changed in Config from '${path.resolve(
+              backstageRootDirectory,
+              'first-dir',
+            )}' to '${path.resolve(backstageRootDirectory, 'second-dir')}'`,
           },
         ],
       });
@@ -204,10 +213,16 @@ describe('plugin-scanner', () => {
       expect(logger.logs).toEqual<Logs>({
         infos: [
           {
-            message: `rootDirectory changed (addDir - ${backstageRootDirectory}/second-dir/second-test-backend-plugin): scanning plugins again`,
+            message: `rootDirectory changed (addDir - ${path.resolve(
+              backstageRootDirectory,
+              'second-dir/second-test-backend-plugin',
+            )}): scanning plugins again`,
           },
           {
-            message: `rootDirectory changed (add - ${backstageRootDirectory}/second-dir/second-test-backend-plugin/package.json): scanning plugins again`,
+            message: `rootDirectory changed (add - ${path.resolve(
+              backstageRootDirectory,
+              'second-dir/second-test-backend-plugin/package.json',
+            )}): scanning plugins again`,
           },
         ],
       });
@@ -263,22 +278,41 @@ describe('plugin-scanner', () => {
         expect(debug).toHaveBeenCalledTimes(4);
       });
 
-      expect(logger.logs).toEqual<Logs>({
-        debugs: [
-          {
-            message: `rootDirectory changed (addDir - ${backstageRootDirectory}/second-dir/second-test-backend-plugin/sub-directory): no need to scan plugins again`,
-          },
-          {
-            message: `rootDirectory changed (add - ${backstageRootDirectory}/second-dir/second-test-backend-plugin/not-package.json): no need to scan plugins again`,
-          },
-          {
-            message: `rootDirectory changed (unlink - ${backstageRootDirectory}/second-dir/second-test-backend-plugin/not-package.json): no need to scan plugins again`,
-          },
-          {
-            message: `rootDirectory changed (unlinkDir - ${backstageRootDirectory}/second-dir/second-test-backend-plugin/sub-directory): no need to scan plugins again`,
-          },
-        ],
-      });
+      const onWindows = path.sep === '\\';
+      // Order of events is not fixed on Windows.
+      // Windows sometimes even adds a 'change' event when a file is unlinked.
+      // So let's not try to tes the detail of received events on Windows
+      if (!onWindows) {
+        // eslint-disable-next-line
+        expect(logger.logs).toEqual<Logs>({
+          debugs: [
+            {
+              message: `rootDirectory changed (addDir - ${path.resolve(
+                backstageRootDirectory,
+                'second-dir/second-test-backend-plugin/sub-directory',
+              )}): no need to scan plugins again`,
+            },
+            {
+              message: `rootDirectory changed (add - ${path.resolve(
+                backstageRootDirectory,
+                'second-dir/second-test-backend-plugin/not-package.json',
+              )}): no need to scan plugins again`,
+            },
+            {
+              message: `rootDirectory changed (unlink - ${path.resolve(
+                backstageRootDirectory,
+                'second-dir/second-test-backend-plugin/not-package.json',
+              )}): no need to scan plugins again`,
+            },
+            {
+              message: `rootDirectory changed (unlinkDir - ${path.resolve(
+                backstageRootDirectory,
+                'second-dir/second-test-backend-plugin/sub-directory',
+              )}): no need to scan plugins again`,
+            },
+          ],
+        });
+      }
       logger.logs = {};
 
       // Now check that removal of some plugin home directory triggers a new scan of plugins
@@ -299,26 +333,39 @@ describe('plugin-scanner', () => {
         expect(scannedPlugins).toEqual([]);
       });
 
-      expect(logger.logs).toEqual<Logs>({
-        infos: [
+      if (!onWindows) {
+        // eslint-disable-next-line
+        expect(logger.logs.infos).toEqual<LogContent[] | undefined>([
           {
-            message: `rootDirectory changed (unlink - ${backstageRootDirectory}/second-dir/second-test-backend-plugin/package.json): scanning plugins again`,
+            message: `rootDirectory changed (unlink - ${path.resolve(
+              backstageRootDirectory,
+              'second-dir/second-test-backend-plugin/package.json',
+            )}): scanning plugins again`,
           },
-        ],
-        errors: [
-          {
-            message: `failed to load dynamic plugin manifest from '${backstageRootDirectory}/second-dir/second-test-backend-plugin'`,
-            meta: {
-              code: 'ENOENT',
-              errno: -2,
-              message: `ENOENT: no such file or directory, open '${backstageRootDirectory}/second-dir/second-test-backend-plugin/package.json'`,
-              name: 'Error',
-              path: `${backstageRootDirectory}/second-dir/second-test-backend-plugin/package.json`,
-              syscall: 'open',
-            },
+        ]);
+      }
+      expect(logger.logs.errors).toEqual<LogContent[] | undefined>([
+        {
+          message: `failed to load dynamic plugin manifest from '${path.resolve(
+            backstageRootDirectory,
+            'second-dir/second-test-backend-plugin',
+          )}'`,
+          meta: {
+            code: 'ENOENT',
+            errno: path.sep === '\\' ? -4058 : -2,
+            message: `ENOENT: no such file or directory, open '${path.resolve(
+              backstageRootDirectory,
+              'second-dir/second-test-backend-plugin/package.json',
+            )}'`,
+            name: 'Error',
+            path: `${path.resolve(
+              backstageRootDirectory,
+              'second-dir/second-test-backend-plugin/package.json',
+            )}`,
+            syscall: 'open',
           },
-        ],
-      });
+        },
+      ]);
       logger.logs = {};
 
       await rm(
@@ -334,13 +381,19 @@ describe('plugin-scanner', () => {
       });
       rootDirectorySubscriber.mockClear();
 
-      expect(logger.logs).toEqual<Logs>({
-        infos: [
-          {
-            message: `rootDirectory changed (unlinkDir - ${backstageRootDirectory}/second-dir/second-test-backend-plugin): scanning plugins again`,
-          },
-        ],
-      });
+      if (!onWindows) {
+        // eslint-disable-next-line
+        expect(logger.logs).toEqual<Logs>({
+          infos: [
+            {
+              message: `rootDirectory changed (unlinkDir - ${path.resolve(
+                backstageRootDirectory,
+                'second-dir/second-test-backend-plugin',
+              )}): scanning plugins again`,
+            },
+          ],
+        });
+      }
       logger.logs = {};
 
       getOptional.mockReturnValue({
@@ -353,8 +406,16 @@ describe('plugin-scanner', () => {
           {
             message: 'failed to apply new config for dynamic plugins',
             meta: {
-              message: `Dynamic plugins under '/somewhere-else/second-dir' cannot access backstage modules in '${backstageRootDirectory}/node_modules'.
-Please add '${backstageRootDirectory}/node_modules' to the 'NODE_PATH' when running the backstage backend.`,
+              message: `Dynamic plugins under '${path.resolve(
+                '/somewhere-else/second-dir',
+              )}' cannot access backstage modules in '${path.resolve(
+                backstageRootDirectory,
+                'node_modules',
+              )}'.
+Please add '${path.resolve(
+                backstageRootDirectory,
+                'node_modules',
+              )}' to the 'NODE_PATH' when running the backstage backend.`,
               name: 'Error',
             },
           },
diff --git a/packages/backend-plugin-manager/src/scanner/plugin-scanner.test.ts b/packages/backend-plugin-manager/src/scanner/plugin-scanner.test.ts
index 25f07baeaa..563cd9eb68 100644
--- a/packages/backend-plugin-manager/src/scanner/plugin-scanner.test.ts
+++ b/packages/backend-plugin-manager/src/scanner/plugin-scanner.test.ts
@@ -20,6 +20,7 @@ import { JsonObject } from '@backstage/types';
 import { Logs, MockedLogger } from '../__testUtils__/testUtils';
 import { ConfigReader } from '@backstage/config';
 import path from 'path';
+import * as url from 'url';
 import { ScannedPluginPackage } from './types';
 
 describe('plugin-scanner', () => {
@@ -73,7 +74,7 @@ describe('plugin-scanner', () => {
             rootDirectory: 'dist-dynamic',
           },
         },
-        expectedRootDirectory: '/backstageRoot/dist-dynamic',
+        expectedRootDirectory: path.resolve('/backstageRoot/dist-dynamic'),
       },
       {
         name: 'valid config with absolute root directory path inside the backstage root',
@@ -90,7 +91,7 @@ describe('plugin-scanner', () => {
             rootDirectory: '/backstageRoot/dist-dynamic',
           },
         },
-        expectedRootDirectory: '/backstageRoot/dist-dynamic',
+        expectedRootDirectory: path.resolve('/backstageRoot/dist-dynamic'),
       },
       {
         name: 'valid config with absolute root directory path outside the backstage root',
@@ -107,8 +108,14 @@ describe('plugin-scanner', () => {
             rootDirectory: '/somewhere/dist-dynamic',
           },
         },
-        expectedError: `Dynamic plugins under '/somewhere/dist-dynamic' cannot access backstage modules in '/backstageRoot/node_modules'.
-Please add '/backstageRoot/node_modules' to the 'NODE_PATH' when running the backstage backend.`,
+        expectedError: `Dynamic plugins under '${path.resolve(
+          '/somewhere/dist-dynamic',
+        )}' cannot access backstage modules in '${path.resolve(
+          '/backstageRoot/node_modules',
+        )}'.
+Please add '${path.resolve(
+          '/backstageRoot/node_modules',
+        )}' to the 'NODE_PATH' when running the backstage backend.`,
       },
       {
         name: 'valid config with absolute root directory path outside the backstage root but with backstage root included in NODE_PATH',
@@ -126,9 +133,13 @@ Please add '/backstageRoot/node_modules' to the 'NODE_PATH' when running the bac
           },
         },
         environment: {
-          NODE_PATH: `/somewhere-else${path.delimiter}/backstageRoot/node_modules${path.delimiter}/anywhere-else`,
+          NODE_PATH: `${path.resolve('/somewhere-else')}${
+            path.delimiter
+          }${path.resolve('/backstageRoot', 'node_modules')}${
+            path.delimiter
+          }${path.resolve('anywhere-else')}`,
         },
-        expectedRootDirectory: '/somewhere/dist-dynamic',
+        expectedRootDirectory: path.resolve('/somewhere/dist-dynamic'),
       },
       {
         name: 'invalid config: dynamicPlugins not an object',
@@ -273,8 +284,8 @@ Please add '/backstageRoot/node_modules' to the 'NODE_PATH' when running the bac
         },
         expectedPluginPackages: [
           {
-            location: new URL(
-              'file:///backstageRoot/dist-dynamic/test-backend-plugin',
+            location: url.pathToFileURL(
+              path.resolve('/backstageRoot/dist-dynamic/test-backend-plugin'),
             ),
             manifest: {
               name: 'test-backend-plugin-dynamic',
@@ -318,8 +329,8 @@ Please add '/backstageRoot/node_modules' to the 'NODE_PATH' when running the bac
         },
         expectedPluginPackages: [
           {
-            location: new URL(
-              'file:///backstageRoot/dist-dynamic/test-backend-plugin',
+            location: url.pathToFileURL(
+              path.resolve('/backstageRoot/dist-dynamic/test-backend-plugin'),
             ),
             manifest: {
               name: 'test-backend-plugin-dynamic',
@@ -347,8 +358,9 @@ Please add '/backstageRoot/node_modules' to the 'NODE_PATH' when running the bac
         expectedLogs: {
           infos: [
             {
-              message:
-                "skipping '/backstageRoot/dist-dynamic/test-backend-plugin' since it is not a directory",
+              message: `skipping '${path.resolve(
+                '/backstageRoot/dist-dynamic/test-backend-plugin',
+              )}' since it is not a directory`,
             },
           ],
         },
@@ -377,8 +389,9 @@ Please add '/backstageRoot/node_modules' to the 'NODE_PATH' when running the bac
         expectedLogs: {
           infos: [
             {
-              message:
-                "skipping '/backstageRoot/dist-dynamic/test-backend-plugin' since it is not a directory",
+              message: `skipping '${path.resolve(
+                '/backstageRoot/dist-dynamic/test-backend-plugin',
+              )}' since it is not a directory`,
             },
           ],
         },
@@ -421,8 +434,8 @@ Please add '/backstageRoot/node_modules' to the 'NODE_PATH' when running the bac
         },
         expectedPluginPackages: [
           {
-            location: new URL(
-              'file:///backstageRoot/dist-dynamic/test-backend-plugin',
+            location: url.pathToFileURL(
+              path.resolve('/backstageRoot/dist-dynamic/test-backend-plugin'),
             ),
             manifest: {
               name: 'test-backend-plugin-dynamic',
@@ -471,8 +484,10 @@ Please add '/backstageRoot/node_modules' to the 'NODE_PATH' when running the bac
         },
         expectedPluginPackages: [
           {
-            location: new URL(
-              'file:///backstageRoot/dist-dynamic/test-backend-plugin/alpha',
+            location: url.pathToFileURL(
+              path.resolve(
+                '/backstageRoot/dist-dynamic/test-backend-plugin/alpha',
+              ),
             ),
             manifest: {
               name: 'test-backend-plugin-dynamic',
@@ -511,8 +526,8 @@ Please add '/backstageRoot/node_modules' to the 'NODE_PATH' when running the bac
         },
         expectedPluginPackages: [
           {
-            location: new URL(
-              'file:///backstageRoot/dist-dynamic/test-backend-plugin',
+            location: url.pathToFileURL(
+              path.resolve('/backstageRoot/dist-dynamic/test-backend-plugin'),
             ),
             manifest: {
               name: 'test-backend-plugin-dynamic',
@@ -525,8 +540,9 @@ Please add '/backstageRoot/node_modules' to the 'NODE_PATH' when running the bac
         expectedLogs: {
           warns: [
             {
-              message:
-                "skipping '/backstageRoot/dist-dynamic/test-backend-plugin/alpha' since it is not a directory",
+              message: `skipping '${path.resolve(
+                '/backstageRoot/dist-dynamic/test-backend-plugin/alpha',
+              )}' since it is not a directory`,
             },
           ],
         },
@@ -567,8 +583,9 @@ Please add '/backstageRoot/node_modules' to the 'NODE_PATH' when running the bac
         expectedLogs: {
           errors: [
             {
-              message:
-                "failed to load dynamic plugin manifest from '/backstageRoot/dist-dynamic/test-backend-plugin/alpha'",
+              message: `failed to load dynamic plugin manifest from '${path.resolve(
+                '/backstageRoot/dist-dynamic/test-backend-plugin/alpha',
+              )}'`,
               meta: {
                 name: 'SyntaxError',
                 message: 'Unexpected token i in JSON at position 0',
@@ -600,8 +617,9 @@ Please add '/backstageRoot/node_modules' to the 'NODE_PATH' when running the bac
         expectedLogs: {
           errors: [
             {
-              message:
-                "failed to load dynamic plugin manifest from '/backstageRoot/dist-dynamic/test-backend-plugin'",
+              message: `failed to load dynamic plugin manifest from '${path.resolve(
+                '/backstageRoot/dist-dynamic/test-backend-plugin',
+              )}'`,
               meta: {
                 name: 'SyntaxError',
                 message: 'Unexpected token i in JSON at position 0',
@@ -637,8 +655,9 @@ Please add '/backstageRoot/node_modules' to the 'NODE_PATH' when running the bac
         expectedLogs: {
           errors: [
             {
-              message:
-                "failed to load dynamic plugin manifest from '/backstageRoot/dist-dynamic/test-backend-plugin'",
+              message: `failed to load dynamic plugin manifest from '${path.resolve(
+                '/backstageRoot/dist-dynamic/test-backend-plugin',
+              )}'`,
               meta: {
                 name: 'Error',
                 message: "field 'backstage.role' not found in 'package.json'",
@@ -674,8 +693,9 @@ Please add '/backstageRoot/node_modules' to the 'NODE_PATH' when running the bac
         expectedLogs: {
           errors: [
             {
-              message:
-                "failed to load dynamic plugin manifest from '/backstageRoot/dist-dynamic/test-backend-plugin'",
+              message: `failed to load dynamic plugin manifest from '${path.resolve(
+                '/backstageRoot/dist-dynamic/test-backend-plugin',
+              )}'`,
               meta: {
                 name: 'Error',
                 message: "field 'main' not found in 'package.json'",
diff --git a/packages/backend-plugin-manager/src/scanner/plugin-scanner.ts b/packages/backend-plugin-manager/src/scanner/plugin-scanner.ts
index bdcf786619..e226a1a8ad 100644
--- a/packages/backend-plugin-manager/src/scanner/plugin-scanner.ts
+++ b/packages/backend-plugin-manager/src/scanner/plugin-scanner.ts
@@ -84,13 +84,13 @@ export class PluginScanner {
     }
 
     const dynamicPluginsRootPath = path.isAbsolute(dynamicPlugins.rootDirectory)
-      ? dynamicPlugins.rootDirectory
+      ? path.resolve(dynamicPlugins.rootDirectory)
       : path.resolve(this.backstageRoot, dynamicPlugins.rootDirectory);
 
     if (
       !path
-        .dirname(path.normalize(dynamicPluginsRootPath))
-        .startsWith(path.normalize(this.backstageRoot))
+        .dirname(dynamicPluginsRootPath)
+        .startsWith(path.resolve(this.backstageRoot))
     ) {
       const nodePath = process.env.NODE_PATH;
       const backstageNodeModules = path.resolve(