diff --git a/.dprint.json b/.dprint.json
index da4351d2c9..b9955f1359 100644
--- a/.dprint.json
+++ b/.dprint.json
@@ -25,6 +25,7 @@
     "cli/tests/testdata/badly_formatted.json",
     "cli/tests/testdata/byte_order_mark.ts",
     "cli/tests/testdata/fmt/*",
+    "cli/tests/testdata/test/markdown_windows.md",
     "cli/tsc/*typescript.js",
     "test_util/std",
     "test_util/wpt",
diff --git a/.gitattributes b/.gitattributes
index 08ef3b672d..1ae3e6d8e1 100644
--- a/.gitattributes
+++ b/.gitattributes
@@ -12,3 +12,6 @@
 # Doesn't include them in the language statistics.
 /cli/tsc/00_typescript.js linguist-vendored
 /cli/dts/* linguist-vendored
+
+# Keep Windows line endings in cross-platform doc check test file
+/cli/tests/testdata/test/markdown_windows.md eol=crlf
diff --git a/cli/tests/integration/fmt_tests.rs b/cli/tests/integration/fmt_tests.rs
index 1adbc8ff81..3046253488 100644
--- a/cli/tests/integration/fmt_tests.rs
+++ b/cli/tests/integration/fmt_tests.rs
@@ -129,7 +129,7 @@ fn fmt_ignore_unexplicit_files() {
 }
 
 itest!(fmt_check_tests_dir {
-  args: "fmt --check ./ --ignore=.test_coverage,fmt/fmt_with_config/",
+  args: "fmt --check ./ --ignore=.test_coverage,fmt/fmt_with_config/,test/markdown_windows.md",
   output: "fmt/expected_fmt_check_tests_dir.out",
   exit_code: 1,
 });
diff --git a/cli/tests/integration/test_tests.rs b/cli/tests/integration/test_tests.rs
index d4412191e6..e5d3fd3584 100644
--- a/cli/tests/integration/test_tests.rs
+++ b/cli/tests/integration/test_tests.rs
@@ -85,6 +85,12 @@ itest!(markdown {
   output: "test/markdown.out",
 });
 
+itest!(markdown_windows {
+  args: "test --doc --allow-all test/markdown_windows.md",
+  exit_code: 1,
+  output: "test/markdown_windows.out",
+});
+
 itest!(text {
   args: "test --doc --allow-all test/text.md",
   exit_code: 0,
diff --git a/cli/tests/testdata/test/markdown_windows.md b/cli/tests/testdata/test/markdown_windows.md
new file mode 100644
index 0000000000..d18dbd1087
--- /dev/null
+++ b/cli/tests/testdata/test/markdown_windows.md
@@ -0,0 +1,31 @@
+# Documentation
+
+The following block does not have a language attribute and should be ignored:
+
+```
+This is a fenced block without attributes, it's invalid and it should be ignored.
+```
+
+The following block should be given a js extension on extraction:
+
+```js
+console.log("js");
+```
+
+The following block should be given a ts extension on extraction:
+
+```ts
+console.log("ts");
+```
+
+The following example contains the ignore attribute and will be ignored:
+
+```ts ignore
+const value: Invalid = "ignored";
+```
+
+The following example will trigger the type-checker to fail:
+
+```ts
+const a: string = 42;
+```
diff --git a/cli/tests/testdata/test/markdown_windows.out b/cli/tests/testdata/test/markdown_windows.out
new file mode 100644
index 0000000000..4810e50cd3
--- /dev/null
+++ b/cli/tests/testdata/test/markdown_windows.out
@@ -0,0 +1,7 @@
+Check [WILDCARD]/test/markdown_windows.md$11-14.js
+Check [WILDCARD]/test/markdown_windows.md$17-20.ts
+Check [WILDCARD]/test/markdown_windows.md$29-32.ts
+error: TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
+const a: string = 42;
+      ^
+    at [WILDCARD]/test/markdown_windows.md$29-32.ts:1:7
diff --git a/cli/tools/test.rs b/cli/tools/test.rs
index fba1782024..ab2f801da7 100644
--- a/cli/tools/test.rs
+++ b/cli/tools/test.rs
@@ -590,7 +590,7 @@ fn extract_files_from_source_comments(
     scope_analysis: false,
   })?;
   let comments = parsed_source.comments().get_vec();
-  let blocks_regex = Regex::new(r"```([^\n]*)\n([\S\s]*?)```")?;
+  let blocks_regex = Regex::new(r"```([^\r\n]*)\r?\n([\S\s]*?)```")?;
   let lines_regex = Regex::new(r"(?:\* ?)(?:\# ?)?(.*)")?;
 
   let files = comments
@@ -630,7 +630,7 @@ fn extract_files_from_fenced_blocks(
     col: 0,
   };
 
-  let blocks_regex = Regex::new(r"```([^\n]*)\n([\S\s]*?)```")?;
+  let blocks_regex = Regex::new(r"```([^\r\n]*)\r?\n([\S\s]*?)```")?;
   let lines_regex = Regex::new(r"(?:\# ?)?(.*)")?;
 
   extract_files_from_regex_blocks(