diff --git a/tests/registry/npm/@denotest/cjs-non-explicit-file/1.0.0/index.js b/tests/registry/npm/@denotest/cjs-non-explicit-file/1.0.0/index.js
new file mode 100644
index 00000000000000..f053ebf7976e37
--- /dev/null
+++ b/tests/registry/npm/@denotest/cjs-non-explicit-file/1.0.0/index.js
@@ -0,0 +1 @@
+module.exports = {};
diff --git a/tests/registry/npm/@denotest/cjs-non-explicit-file/1.0.0/package.json b/tests/registry/npm/@denotest/cjs-non-explicit-file/1.0.0/package.json
new file mode 100644
index 00000000000000..79e0f0e1defdf3
--- /dev/null
+++ b/tests/registry/npm/@denotest/cjs-non-explicit-file/1.0.0/package.json
@@ -0,0 +1,5 @@
+{
+  "name": "@denotest/cjs-non-explicit-file",
+  "version": "1.0.0",
+  "main": "index.js"
+}
\ No newline at end of file
diff --git a/tests/registry/npm/@denotest/cjs-non-explicit-file/1.0.0/server.js b/tests/registry/npm/@denotest/cjs-non-explicit-file/1.0.0/server.js
new file mode 100644
index 00000000000000..ef4ef1ef23580c
--- /dev/null
+++ b/tests/registry/npm/@denotest/cjs-non-explicit-file/1.0.0/server.js
@@ -0,0 +1 @@
+module.exports = require("./server.node");
diff --git a/tests/registry/npm/@denotest/cjs-non-explicit-file/1.0.0/server.node.js b/tests/registry/npm/@denotest/cjs-non-explicit-file/1.0.0/server.node.js
new file mode 100644
index 00000000000000..6e9f28dfbf2ef5
--- /dev/null
+++ b/tests/registry/npm/@denotest/cjs-non-explicit-file/1.0.0/server.node.js
@@ -0,0 +1,3 @@
+module.exports["server"] = function () {
+  return 1;
+};
diff --git a/tests/specs/npm/sub_paths_cjs_import_faillure/__test__.jsonc b/tests/specs/npm/sub_paths_cjs_import_faillure/__test__.jsonc
new file mode 100644
index 00000000000000..68de201ff8e166
--- /dev/null
+++ b/tests/specs/npm/sub_paths_cjs_import_faillure/__test__.jsonc
@@ -0,0 +1,15 @@
+{
+  "steps": [{
+    "args": "run --quiet sub_paths_cjs_import_faillure/main1.js",
+    "output": "sub_paths_cjs_import_faillure/main1.out",
+    "exitCode": 1
+  }, {
+    "args": "run --quiet sub_paths_cjs_import_faillure/main2.js",
+    "output": "sub_paths_cjs_import_faillure/main2.out",
+    "exitCode": 1
+  }, {
+    "args": "run --quiet sub_paths_cjs_import_faillure/main3.js",
+    "output": "sub_paths_cjs_import_faillure/main3.out",
+    "exitCode": 1
+  }]
+}
diff --git a/tests/specs/npm/sub_paths_cjs_import_faillure/sub_paths_cjs_import_faillure/main1.js b/tests/specs/npm/sub_paths_cjs_import_faillure/sub_paths_cjs_import_faillure/main1.js
new file mode 100644
index 00000000000000..4313cc1551b127
--- /dev/null
+++ b/tests/specs/npm/sub_paths_cjs_import_faillure/sub_paths_cjs_import_faillure/main1.js
@@ -0,0 +1,2 @@
+import Server from "npm:@denotest/cjs-non-explicit-file@1.0.0/server";
+console.log(Server);
diff --git a/tests/specs/npm/sub_paths_cjs_import_faillure/sub_paths_cjs_import_faillure/main1.out b/tests/specs/npm/sub_paths_cjs_import_faillure/sub_paths_cjs_import_faillure/main1.out
new file mode 100644
index 00000000000000..a370ab322a3975
--- /dev/null
+++ b/tests/specs/npm/sub_paths_cjs_import_faillure/sub_paths_cjs_import_faillure/main1.out
@@ -0,0 +1,5 @@
+error: Unable to load [WILDCARD]server imported from [WILDCARD]main1.js
+Did you mean to import "npm:@denotest/cjs-non-explicit-file@1.0.0/server.js"?
+
+Caused by:
+[WILDCARD]
diff --git a/tests/specs/npm/sub_paths_cjs_import_faillure/sub_paths_cjs_import_faillure/main2.js b/tests/specs/npm/sub_paths_cjs_import_faillure/sub_paths_cjs_import_faillure/main2.js
new file mode 100644
index 00000000000000..e3b361d7f55c9b
--- /dev/null
+++ b/tests/specs/npm/sub_paths_cjs_import_faillure/sub_paths_cjs_import_faillure/main2.js
@@ -0,0 +1,2 @@
+import Server from "npm:@denotest/cjs-non-explicit-file@1.0.0/server.node";
+console.log(Server);
diff --git a/tests/specs/npm/sub_paths_cjs_import_faillure/sub_paths_cjs_import_faillure/main2.out b/tests/specs/npm/sub_paths_cjs_import_faillure/sub_paths_cjs_import_faillure/main2.out
new file mode 100644
index 00000000000000..a2d026488e2b16
--- /dev/null
+++ b/tests/specs/npm/sub_paths_cjs_import_faillure/sub_paths_cjs_import_faillure/main2.out
@@ -0,0 +1,5 @@
+error: Unable to load [WILDCARD]server.node imported from [WILDCARD]main2.js
+Did you mean to import "npm:@denotest/cjs-non-explicit-file@1.0.0/server.node.js"?
+
+Caused by:
+[WILDCARD]
diff --git a/tests/specs/npm/sub_paths_cjs_import_faillure/sub_paths_cjs_import_faillure/main3.js b/tests/specs/npm/sub_paths_cjs_import_faillure/sub_paths_cjs_import_faillure/main3.js
new file mode 100644
index 00000000000000..a8c17fd810ed23
--- /dev/null
+++ b/tests/specs/npm/sub_paths_cjs_import_faillure/sub_paths_cjs_import_faillure/main3.js
@@ -0,0 +1,3 @@
+// deno-fmt-ignore
+const Server = await import("npm:@denotest/cjs-non-explicit-file@1.0.0/server");
+console.log(Server);
diff --git a/tests/specs/npm/sub_paths_cjs_import_faillure/sub_paths_cjs_import_faillure/main3.out b/tests/specs/npm/sub_paths_cjs_import_faillure/sub_paths_cjs_import_faillure/main3.out
new file mode 100644
index 00000000000000..e9d099a8a63505
--- /dev/null
+++ b/tests/specs/npm/sub_paths_cjs_import_faillure/sub_paths_cjs_import_faillure/main3.out
@@ -0,0 +1,7 @@
+error: Uncaught (in promise) TypeError: Unable to load [WILDCARD]server imported from [WILDCARD]main3.js
+Did you mean to import "npm:@denotest/cjs-non-explicit-file@1.0.0/server.js"?
+  Caused by:
+[WILDCARD]
+const Server = await import("npm:@denotest/cjs-non-explicit-file@1.0.0/server");
+               ^
+    at async [WILDCARD]main3.js:[WILDCARD]