diff --git a/src/convert/replacements.ts b/src/convert/replacements.ts
index b134e1ddfc..2ad1fd3eda 100644
--- a/src/convert/replacements.ts
+++ b/src/convert/replacements.ts
@@ -6,6 +6,7 @@
  */
 import { readFile } from 'fs/promises';
 import { Transform, Readable } from 'stream';
+import { sep, posix } from 'path';
 import { Lifecycle, Messages, SfProject } from '@salesforce/core';
 import * as minimatch from 'minimatch';
 import { Env } from '@salesforce/kit';
@@ -194,7 +195,7 @@ export const getReplacements = async (
 export const matchesFile = (f: string, r: ReplacementConfig): boolean =>
   // filenames will be absolute.  We don't have convenient access to the pkgDirs,
   // so we need to be more open than an exact match
-  Boolean((r.filename && f.endsWith(r.filename)) || (r.glob && minimatch(f, `**/${r.glob}`)));
+  Boolean((r.filename && posixifyPaths(f).endsWith(r.filename)) || (r.glob && minimatch(f, `**/${r.glob}`)));
 
 /**
  * Regardless of any components, return the ReplacementConfig that are valid with the current env.
@@ -228,3 +229,5 @@ export const stringToRegex = (input: string): RegExp =>
   // being overly conservative
   // eslint-disable-next-line no-useless-escape
   new RegExp(input.replace(/[-\/\\^$*+?.()|[\]{}]/g, '\\$&'), 'g');
+
+const posixifyPaths = (f: string): string => f.split(sep).join(posix.sep);
diff --git a/test/convert/replacements.test.ts b/test/convert/replacements.test.ts
index c3bd82934c..9e02136352 100644
--- a/test/convert/replacements.test.ts
+++ b/test/convert/replacements.test.ts
@@ -18,6 +18,10 @@ describe('file matching', () => {
     expect(matchesFile('foo', { filename: 'foo', ...base })).to.be.true;
     expect(matchesFile('bar', { filename: 'foo', ...base })).to.not.be.true;
   });
+  it('paths with separators to cover possibility of windows paths', () => {
+    expect(matchesFile(path.join('foo', 'bar'), { filename: 'foo/bar', ...base })).to.be.true;
+    expect(matchesFile(path.join('foo', 'bar'), { filename: 'foo/baz', ...base })).to.not.be.true;
+  });
   it('file matches glob (posix paths)', () => {
     expect(matchesFile('foo/bar', { glob: 'foo/**', ...base })).to.be.true;
     expect(matchesFile('foo/bar', { glob: 'foo/*', ...base })).to.be.true;