diff --git a/cli/main.rs b/cli/main.rs
index 6069f44792..93bae02206 100644
--- a/cli/main.rs
+++ b/cli/main.rs
@@ -1026,17 +1026,19 @@ async fn test_command(
 
     // TODO(caspervonb) clean this up.
     let resolver = |changed: Option<Vec<PathBuf>>| {
-      let doc_modules_result = test_runner::collect_test_module_specifiers(
-        include.clone(),
-        &cwd,
-        fs_util::is_supported_ext,
-      );
-
-      let test_modules_result = test_runner::collect_test_module_specifiers(
-        include.clone(),
-        &cwd,
-        tools::test_runner::is_supported,
-      );
+      let test_modules_result = if doc {
+        test_runner::collect_test_module_specifiers(
+          include.clone(),
+          &cwd,
+          fs_util::is_supported_ext,
+        )
+      } else {
+        test_runner::collect_test_module_specifiers(
+          include.clone(),
+          &cwd,
+          tools::test_runner::is_supported,
+        )
+      };
 
       let paths_to_watch = paths_to_watch.clone();
       let paths_to_watch_clone = paths_to_watch.clone();
@@ -1045,8 +1047,6 @@ async fn test_command(
       let program_state = program_state.clone();
       let files_changed = changed.is_some();
       async move {
-        let doc_modules = if doc { doc_modules_result? } else { Vec::new() };
-
         let test_modules = test_modules_result?;
 
         let mut paths_to_watch = paths_to_watch_clone;
@@ -1072,12 +1072,6 @@ async fn test_command(
           .await?;
         let graph = builder.get_graph();
 
-        for specifier in doc_modules {
-          if let Ok(path) = specifier.to_file_path() {
-            paths_to_watch.push(path);
-          }
-        }
-
         for specifier in test_modules {
           fn get_dependencies<'a>(
             graph: &'a module_graph::Graph,
@@ -1165,15 +1159,49 @@ async fn test_command(
       })
     };
 
-    file_watcher::watch_func(
-      resolver,
-      |modules_to_reload| {
+    let operation = |modules_to_reload: Vec<ModuleSpecifier>| {
+      let cwd = cwd.clone();
+      let filter = filter.clone();
+      let include = include.clone();
+      let lib = lib.clone();
+      let permissions = permissions.clone();
+      let program_state = program_state.clone();
+
+      async move {
+        let doc_modules = if doc {
+          test_runner::collect_test_module_specifiers(
+            include.clone(),
+            &cwd,
+            fs_util::is_supported_ext,
+          )?
+        } else {
+          Vec::new()
+        };
+
+        let doc_modules_to_reload = doc_modules
+          .iter()
+          .filter(|specifier| modules_to_reload.contains(specifier))
+          .cloned()
+          .collect();
+
+        let test_modules = test_runner::collect_test_module_specifiers(
+          include.clone(),
+          &cwd,
+          tools::test_runner::is_supported,
+        )?;
+
+        let test_modules_to_reload = test_modules
+          .iter()
+          .filter(|specifier| modules_to_reload.contains(specifier))
+          .cloned()
+          .collect();
+
         test_runner::run_tests(
           program_state.clone(),
           permissions.clone(),
           lib.clone(),
-          modules_to_reload.clone(),
-          modules_to_reload,
+          doc_modules_to_reload,
+          test_modules_to_reload,
           no_run,
           fail_fast,
           quiet,
@@ -1182,11 +1210,13 @@ async fn test_command(
           shuffle,
           concurrent_jobs,
         )
-        .map(|res| res.map(|_| ()))
-      },
-      "Test",
-    )
-    .await?;
+        .await?;
+
+        Ok(())
+      }
+    };
+
+    file_watcher::watch_func(resolver, operation, "Test").await?;
   } else {
     let doc_modules = if doc {
       test_runner::collect_test_module_specifiers(
diff --git a/cli/tests/integration/watcher_tests.rs b/cli/tests/integration/watcher_tests.rs
index 3e9aa563a7..ed574a0bf1 100644
--- a/cli/tests/integration/watcher_tests.rs
+++ b/cli/tests/integration/watcher_tests.rs
@@ -595,3 +595,77 @@ fn test_watch() {
   child.kill().unwrap();
   drop(t);
 }
+
+// TODO(bartlomieju): flaky (https://github.com/denoland/deno/issues/10552)
+#[ignore]
+#[test]
+fn test_watch_doc() {
+  macro_rules! assert_contains {
+        ($string:expr, $($test:expr),+) => {
+          let string = $string; // This might be a function call or something
+          if !($(string.contains($test))||+) {
+            panic!("{:?} does not contain any of {:?}", string, [$($test),+]);
+          }
+        }
+      }
+
+  let t = TempDir::new().expect("tempdir fail");
+
+  let mut child = util::deno_cmd()
+    .current_dir(util::root_path())
+    .arg("test")
+    .arg("--watch")
+    .arg("--doc")
+    .arg("--unstable")
+    .arg(&t.path())
+    .env("NO_COLOR", "1")
+    .stdout(std::process::Stdio::piped())
+    .stderr(std::process::Stdio::piped())
+    .spawn()
+    .expect("failed to spawn script");
+
+  let stdout = child.stdout.as_mut().unwrap();
+  let mut stdout_lines =
+    std::io::BufReader::new(stdout).lines().map(|r| r.unwrap());
+  let stderr = child.stderr.as_mut().unwrap();
+  let mut stderr_lines =
+    std::io::BufReader::new(stderr).lines().map(|r| r.unwrap());
+
+  assert_contains!(
+    stdout_lines.next().unwrap(),
+    "No matching test modules found"
+  );
+
+  wait_for_process_finished("Test", &mut stderr_lines);
+
+  let foo_file = t.path().join("foo.ts");
+  std::fs::write(
+    &foo_file,
+    r#"
+    export default function foo() {}
+  "#,
+  )
+  .expect("error writing file");
+
+  std::fs::write(
+    &foo_file,
+    r#"
+    /**
+     * ```ts
+     * import foo from "./foo.ts";
+     * ```
+     */
+    export default function foo() {}
+  "#,
+  )
+  .expect("error writing file");
+
+  // We only need to scan for a Check file://.../foo.ts$3-6 line that
+  // corresponds to the documentation block being type-checked.
+  assert_contains!(skip_restarting_line(stderr_lines), "foo.ts$3-6");
+
+  assert!(child.try_wait().unwrap().is_none());
+  child.kill().unwrap();
+
+  drop(t);
+}