diff --git a/lib/internal/source_map/source_map_cache.js b/lib/internal/source_map/source_map_cache.js
index 2813da21dfdc63..b4b1d8b33b566b 100644
--- a/lib/internal/source_map/source_map_cache.js
+++ b/lib/internal/source_map/source_map_cache.js
@@ -39,6 +39,7 @@ const kLeadingProtocol = /^\w+:\/\//;
 const kSourceMappingURLMagicComment = /\/[*/]#\s+sourceMappingURL=(?<sourceMappingURL>[^\s]+)/g;
 const kSourceURLMagicComment = /\/[*/]#\s+sourceURL=(?<sourceURL>[^\s]+)/g;
 
+const { isAbsolute } = require('path');
 const { fileURLToPath, pathToFileURL, URL } = require('internal/url');
 
 let SourceMap;
@@ -254,6 +255,9 @@ function sourceMapFromDataUrl(sourceURL, url) {
 function sourcesToAbsolute(baseURL, data) {
   data.sources = data.sources.map((source) => {
     source = (data.sourceRoot || '') + source;
+    if (isAbsolute(source)) {
+      return pathToFileURL(source).href;
+    }
     return new URL(source, baseURL).href;
   });
   // The sources array is now resolved to absolute URLs, sourceRoot should
diff --git a/test/fixtures/source-map/ts-node-win32.js b/test/fixtures/source-map/ts-node-win32.js
new file mode 100644
index 00000000000000..3c1ab9363544d2
--- /dev/null
+++ b/test/fixtures/source-map/ts-node-win32.js
@@ -0,0 +1,10 @@
+function foo(str) {
+    return str;
+}
+foo('noop');
+// To recreate (only on windows):
+//
+// const filePath = require.resolve('./test/fixtures/source-map/ts-node.ts');
+// const compiled = require('ts-node').create({ transpileOnly: true }).compile(fs.readFileSync(filePath, 'utf8'), filePath);
+// fs.writeFileSync('test/fixtures/source-map/ts-node-win32.js', compiled);
+//# sourceMappingURL=data:application/json;charset=utf-8;base64,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
\ No newline at end of file
diff --git a/test/fixtures/source-map/ts-node.ts b/test/fixtures/source-map/ts-node.ts
new file mode 100644
index 00000000000000..ac0a7293915695
--- /dev/null
+++ b/test/fixtures/source-map/ts-node.ts
@@ -0,0 +1,11 @@
+function foo(str: string) {
+  return str;
+}
+
+foo('noop');
+
+// To recreate (only on windows):
+//
+// const filePath = require.resolve('./test/fixtures/source-map/ts-node.ts');
+// const compiled = require('ts-node').create({ transpileOnly: true }).compile(fs.readFileSync(filePath, 'utf8'), filePath);
+// fs.writeFileSync('test/fixtures/source-map/ts-node-win32.js', compiled);
diff --git a/test/parallel/test-source-map-enable.js b/test/parallel/test-source-map-enable.js
index 5038aff360e518..e7d24d9e6da022 100644
--- a/test/parallel/test-source-map-enable.js
+++ b/test/parallel/test-source-map-enable.js
@@ -289,6 +289,30 @@ function nextdir() {
   assert.match(output.stderr.toString(), /at functionC.*10:3/);
 }
 
+// Properly converts windows absolute paths to absolute URLs
+// Refs: https://github.com/nodejs/node/issues/50523
+// Refs: https://github.com/TypeStrong/ts-node/issues/1769
+{
+  const coverageDirectory = nextdir();
+  const output = spawnSync(process.execPath, [
+    require.resolve('../fixtures/source-map/ts-node-win32.js'),
+  ], { env: { ...process.env, NODE_V8_COVERAGE: coverageDirectory } });
+  assert.strictEqual(output.status, 0);
+  assert.strictEqual(output.stderr.toString(), '');
+  const sourceMap = getSourceMapFromCache(
+    'ts-node-win32.js',
+    coverageDirectory
+  );
+  // base64 JSON should have been decoded, the D: in the sources field should
+  // have been taken as the drive letter on Windows, the scheme on POSIX.
+  assert.strictEqual(
+    sourceMap.data.sources[0],
+    common.isWindows ?
+      'file:///D:/workspaces/node/test/fixtures/source-map/ts-node.ts' :
+      'd:/workspaces/node/test/fixtures/source-map/ts-node.ts'
+  );
+}
+
 // Stores and applies source map associated with file that throws while
 // being required.
 {