diff --git a/src/js_printer.zig b/src/js_printer.zig
index ebe08d3d59..c510555bba 100644
--- a/src/js_printer.zig
+++ b/src/js_printer.zig
@@ -3685,6 +3685,8 @@ fn NewPrinter(
 
             switch (stmt.data) {
                 .s_comment => |s| {
+                    p.printIndent();
+                    p.addSourceMapping(stmt.loc);
                     p.printIndentedComment(s.text);
                 },
                 .s_function => |s| {
@@ -5146,16 +5148,26 @@ fn NewPrinter(
             if (strings.startsWith(text, "/*")) {
                 // Re-indent multi-line comments
                 while (strings.indexOfChar(text, '\n')) |newline_index| {
+
+                    // Skip over \r if it precedes \n
+                    if (newline_index > 0 and text[newline_index - 1] == '\r') {
+                        p.print(text[0 .. newline_index - 1]);
+                        p.print("\n");
+                    } else {
+                        p.print(text[0 .. newline_index + 1]);
+                    }
                     p.printIndent();
-                    p.print(text[0 .. newline_index + 1]);
+
                     text = text[newline_index + 1 ..];
                 }
-                p.printIndent();
                 p.print(text);
                 p.printNewline();
             } else {
                 // Print a mandatory newline after single-line comments
-                p.printIndent();
+                if (text.len > 0 and text[text.len - 1] == '\r') {
+                    text = text[0 .. text.len - 1];
+                }
+
                 p.print(text);
                 p.print("\n");
             }
diff --git a/test/bundler/bundler_comments.test.ts b/test/bundler/bundler_comments.test.ts
index 7abcd563bc..540129c5ce 100644
--- a/test/bundler/bundler_comments.test.ts
+++ b/test/bundler/bundler_comments.test.ts
@@ -1,4 +1,5 @@
-import { describe } from "bun:test";
+import { describe, expect } from "bun:test";
+import { SourceMap } from "node:module";
 import { itBundled } from "./expectBundled";
 
 describe("single-line comments", () => {
@@ -351,3 +352,42 @@ describe("single-line comments", () => {
     },
   });
 });
+
+describe("multi-line comments", () => {
+  itBundled("comment with \\r\\n has sourcemap", {
+    files: {
+      "/entry.js": "/*!\r\n * Legal comment line 1\r\n * Legal comment line 2\r\n */\r\nexport const x = 1;",
+    },
+    sourceMap: "external",
+    onAfterBundle(api) {
+      const output = api.readFile("/out.js");
+      const sourcemapContent = api.readFile("/out.js.map");
+      const sourcemap = JSON.parse(sourcemapContent);
+      const sm = new SourceMap(sourcemap);
+
+      // Find the multi-line legal comment in the output
+      const outputLines = output.split("\n");
+      let commentLineIndex = -1;
+      for (let i = 0; i < outputLines.length; i++) {
+        if (outputLines[i].includes("Legal comment")) {
+          commentLineIndex = i;
+          break;
+        }
+      }
+
+      expect(commentLineIndex).toBeGreaterThanOrEqual(0);
+
+      // The multi-line legal comment should have a sourcemap entry
+      const entry = sm.findEntry(commentLineIndex, 0);
+
+      // Verify we found a mapping for the comment
+      expect(entry).toBeTruthy();
+      expect(Object.keys(entry).length).toBeGreaterThan(0);
+
+      // The mapping should point back to the original source
+      expect(entry!.originalSource!).toContain("entry.js");
+      expect(typeof entry.originalLine).toBe("number");
+      expect(entry.originalLine).toBeGreaterThanOrEqual(0);
+    },
+  });
+});
diff --git a/test/no-validate-exceptions.txt b/test/no-validate-exceptions.txt
index 2d31e15934..67563774a7 100644
--- a/test/no-validate-exceptions.txt
+++ b/test/no-validate-exceptions.txt
@@ -49,6 +49,7 @@ test/bundler/esbuild/default.test.ts
 test/cli/install/bun-repl.test.ts
 test/js/third_party/astro/astro-post.test.js
 test/regression/issue/ctrl-c.test.ts
+test/bundler/bundler_comments.test.ts
 test/js/node/test/parallel/test-fs-promises-file-handle-readLines.mjs
 
 # trips asan on my macos test machine