diff --git a/src/sourcemap/Chunk.rs b/src/sourcemap/Chunk.rs
index 899e5671c01f..79e167d9dca3 100644
--- a/src/sourcemap/Chunk.rs
+++ b/src/sourcemap/Chunk.rs
@@ -568,12 +568,9 @@ impl NewBuilder<'_, VLQSourceMap> {
                 }
                 // '\r', '\n', U+2028, U+2029
                 0x0D | 0x0A | 0x2028 | 0x2029 => {
-                    // windows newline
-                    if c == 0x0D {
-                        let newline_check = self.last_generated_update as usize + i + 1;
-                        if newline_check < output.len() && output[newline_check] == b'\n' {
-                            continue;
-                        }
+                    // windows newline: `i` already points at the byte after the '\r'
+                    if c == 0x0D && i < n && slice[i] == b'\n' {
+                        continue;
                     }
 
                     // If we're about to move to the next line and the previous line didn't have
diff --git a/test/bundler/bundler_comments.test.ts b/test/bundler/bundler_comments.test.ts
index c05527343bf9..30fc55b72126 100644
--- a/test/bundler/bundler_comments.test.ts
+++ b/test/bundler/bundler_comments.test.ts
@@ -1,4 +1,5 @@
 import { describe, expect } from "bun:test";
+import { readFileSync } from "node:fs";
 import { SourceMap } from "node:module";
 import { itBundled } from "./expectBundled";
 
@@ -391,6 +392,57 @@ describe("multi-line comments", () => {
     },
   });
 
+  // JS engines count a lone "\r" as a line terminator and "\r\n" as a single
+  // one, so the generated lines in the map have to be counted the same way for
+  // stack traces to remap. A legal comment is printed verbatim apart from its
+  // "\r\n"s becoming "\n", and an inlined enum member is followed by a comment
+  // holding its name; those are how these terminators end up in the output.
+  function lineOf(code: string, needle: string) {
+    const index = code.split(/\r\n|\r|\n/).findIndex(line => line.includes(needle));
+    expect(index).toBeGreaterThanOrEqual(0);
+    return index;
+  }
+  const terminatorCases = [
+    {
+      name: "lone CR in a legal comment starts a new generated line in the sourcemap",
+      file: "/entry.js",
+      // One character between the "\r" and the "\n" is the shape the builder used to miss.
+      entry: '/*! a\rb\nc */\nconsole.log("after comment");\nconsole.log("next line");\n',
+      printed: "/*! a\rb\nc */",
+      needles: ['"after comment"', '"next line"'],
+    },
+    {
+      name: "CRLF left in a legal comment counts as one generated line in the sourcemap",
+      file: "/entry.js",
+      entry: '/*! a\r\r\nb */\nconsole.log("after comment");\nconsole.log("next line");\n',
+      printed: "/*! a\r\nb */",
+      needles: ['"after comment"', '"next line"'],
+    },
+    {
+      name: "CRLF in an inlined enum member comment counts as one generated line in the sourcemap",
+      file: "/entry.ts",
+      entry: 'enum E { "a\\r\\nb" = 1 }\nconsole.log(E["a\\r\\nb"]);\nconsole.log("next line");\n',
+      printed: "1 /* a\r\nb */",
+      needles: ['"next line"'],
+    },
+  ];
+  for (const { name, file, entry, printed, needles } of terminatorCases) {
+    itBundled(name, {
+      files: { [file]: entry },
+      sourceMap: "external",
+      onAfterBundle(api) {
+        // api.readFile() normalizes CRLF, so read the output directly.
+        const output = readFileSync(api.outfile, "utf8");
+        expect(output).toContain(printed);
+        const map = new SourceMap(JSON.parse(readFileSync(api.outfile + ".map", "utf8")));
+        // The generated line each needle ends up on must map back to the line it is on in the entry.
+        expect(needles.map(needle => [needle, map.findEntry(lineOf(output, needle), 0).originalLine])).toEqual(
+          needles.map(needle => [needle, lineOf(entry, needle)]),
+        );
+      },
+    });
+  }
+
   // The lexer skips >=512-byte block comment bodies with SIMD; these verify
   // large comments end-to-end (legal comment preservation, ASI, output code).
   itBundled("large legal comment is preserved and does not corrupt the code after it", {
diff --git a/test/js/bun/sourcemap/internal-sourcemap.test.ts b/test/js/bun/sourcemap/internal-sourcemap.test.ts
index b8efdae7770b..3934cefa9419 100644
--- a/test/js/bun/sourcemap/internal-sourcemap.test.ts
+++ b/test/js/bun/sourcemap/internal-sourcemap.test.ts
@@ -191,6 +191,31 @@ describe("InternalSourceMap", () => {
     expect(exited).toBe(0);
   });
 
+  // The generated lines counted while building the map have to agree with what
+  // JSC reports: a lone "\r" is a line terminator and "\r\n" is a single one. A
+  // legal comment is printed verbatim apart from its "\r\n"s becoming "\n", so
+  // it is how either reaches the transpiled code ("\r\r\n" comes out as "\r\n").
+  describe("line terminators inside a legal comment", () => {
+    async function remappedLines(index: string) {
+      const { stdout, stderr, exited } = await run({ "index.ts": index });
+      expect(stderr).toBe("");
+      expect(exited).toBe(0);
+      return [...stdout.matchAll(/index\.ts:(\d+):\d+/g)].map(m => Number(m[1]));
+    }
+
+    test("a lone CR starts a new line", async () => {
+      // Lines: 1 "/*! a", 2 "b", 3 "c */", 4 the Error, 5 console.log.
+      const index = '/*! a\rb\nc */\nconst err = new Error("x");\nconsole.log(err.stack);\n';
+      expect(await remappedLines(index)).toEqual([4]);
+    });
+
+    test("a CRLF is a single line break", async () => {
+      // Lines: 1 "/*! a", 2 "", 3 "b */", 4 console.log("before"), 5 the Error, 6 console.log.
+      const index = '/*! a\r\r\nb */\nconsole.log("before");\nconst err = new Error("x");\nconsole.log(err.stack);\n';
+      expect(await remappedLines(index)).toEqual([5]);
+    });
+  });
+
   test("FindCache eviction (>16 distinct windows in one stack)", async () => {
     // 20 functions spread ~125 lines apart in a single file. With ~6 mappings
     // per padding line that's ~750 mappings between calls -> each frame lands