diff --git a/cli/tools/doc.rs b/cli/tools/doc.rs
index 197596167fecea..9a24e458ac9e9b 100644
--- a/cli/tools/doc.rs
+++ b/cli/tools/doc.rs
@@ -209,10 +209,14 @@ pub async fn doc(
       Default::default()
     };
 
+    let mut main_entrypoint = None;
+
     let rewrite_map =
       if let Some(config_file) = cli_options.start_dir.maybe_deno_json() {
         let config = config_file.to_exports_config()?;
 
+        main_entrypoint = config.get_resolved(".").ok().flatten();
+
         let rewrite_map = config
           .clone()
           .into_map()
@@ -240,6 +244,7 @@ pub async fn doc(
       html_options,
       deno_ns,
       rewrite_map,
+      main_entrypoint,
     )
   } else {
     let modules_len = doc_nodes_by_url.len();
@@ -383,6 +388,7 @@ fn generate_docs_directory(
   html_options: &DocHtmlFlag,
   deno_ns: std::collections::HashMap<Vec<String>, Option<Rc<ShortPath>>>,
   rewrite_map: Option<IndexMap<ModuleSpecifier, String>>,
+  main_entrypoint: Option<ModuleSpecifier>,
 ) -> Result<(), AnyError> {
   let cwd = std::env::current_dir().context("Failed to get CWD")?;
   let output_dir_resolved = cwd.join(&html_options.output);
@@ -415,7 +421,7 @@ fn generate_docs_directory(
 
   let options = deno_doc::html::GenerateOptions {
     package_name: html_options.name.clone(),
-    main_entrypoint: None,
+    main_entrypoint,
     rewrite_map,
     href_resolver: Rc::new(DocResolver {
       deno_ns,
diff --git a/tests/specs/doc/html/__test__.jsonc b/tests/specs/doc/html/__test__.jsonc
index 5114127cd61a09..78ced63744e82a 100644
--- a/tests/specs/doc/html/__test__.jsonc
+++ b/tests/specs/doc/html/__test__.jsonc
@@ -1,12 +1,21 @@
 {
   "tempDir": true,
-  "args": [
-    "doc",
-    "--html",
-    "--name=MyLib",
-    "--output=temp_dir_path_here",
-    "referenced_private_types_fixed.ts"
-  ],
-  "output": "[WILDCARD]",
-  "exitCode": 0
+  "steps": [
+    {
+      "args": [
+        "doc",
+        "--html",
+        "--name=MyLib",
+        "a.ts",
+        "b.ts"
+      ],
+      "output": "Written 23 files to \"./docs/\"\n",
+      "exitCode": 0
+    },
+    {
+      "args": "run --allow-read check_file.ts",
+      "output": "",
+      "exitCode": 0
+    }
+  ]
 }
diff --git a/tests/specs/doc/html/referenced_private_types_fixed.ts b/tests/specs/doc/html/a.ts
similarity index 100%
rename from tests/specs/doc/html/referenced_private_types_fixed.ts
rename to tests/specs/doc/html/a.ts
diff --git a/tests/specs/doc/html/b.ts b/tests/specs/doc/html/b.ts
new file mode 100644
index 00000000000000..bb385369923e67
--- /dev/null
+++ b/tests/specs/doc/html/b.ts
@@ -0,0 +1,11 @@
+/** Doc comment */
+export interface MyInterface2 {
+  /** Doc comment */
+  prop?: string;
+}
+
+/** Doc comment */
+export class MyClass2 {
+  /** Doc comment */
+  prop: MyInterface2 = {};
+}
diff --git a/tests/specs/doc/html/check_file.ts b/tests/specs/doc/html/check_file.ts
new file mode 100644
index 00000000000000..7d2fdeff5f6256
--- /dev/null
+++ b/tests/specs/doc/html/check_file.ts
@@ -0,0 +1,5 @@
+const content = Deno.readTextFileSync("./docs/index.html");
+
+if (content.includes("..")) {
+  throw new Error();
+}
diff --git a/tests/specs/doc/html/deno.json b/tests/specs/doc/html/deno.json
new file mode 100644
index 00000000000000..b466b28003a728
--- /dev/null
+++ b/tests/specs/doc/html/deno.json
@@ -0,0 +1,5 @@
+{
+  "exports": {
+    ".": "./a.ts"
+  }
+}