diff --git a/denops/@denops-private/service.ts b/denops/@denops-private/service.ts
index 0e1f1392..b49e1427 100644
--- a/denops/@denops-private/service.ts
+++ b/denops/@denops-private/service.ts
@@ -151,12 +151,7 @@ class Plugin {
     } catch (e) {
       // Show a warning message when Deno module cache issue is detected
       // https://github.com/vim-denops/denops.vim/issues/358
-      if (
-        e instanceof TypeError &&
-        e.message.startsWith(
-          "Could not find constraint in the list of versions: ",
-        )
-      ) {
+      if (isDenoCacheIssueError(e)) {
         console.warn("*".repeat(80));
         console.warn(`Deno module cache issue is detected.`);
         console.warn(
@@ -200,6 +195,18 @@ function resolveScriptUrl(script: string): string {
   }
 }
 
+// See https://github.com/vim-denops/denops.vim/issues/358 for details
+function isDenoCacheIssueError(e: unknown): boolean {
+  const expects = [
+    "Could not find constraint in the list of versions: ", // Deno 1.40?
+    "Could not find version of ", // Deno 1.38
+  ] as const;
+  if (e instanceof TypeError) {
+    return expects.some((expect) => e.message.startsWith(expect));
+  }
+  return false;
+}
+
 // NOTE:
 // Vim/Neovim does not handle JavaScript Error instance thus use string instead
 function toVimError(err: unknown): string {
diff --git a/denops/@denops-private/service_test.ts b/denops/@denops-private/service_test.ts
index 3842da4b..511a28d2 100644
--- a/denops/@denops-private/service_test.ts
+++ b/denops/@denops-private/service_test.ts
@@ -22,6 +22,9 @@ const scriptInvalid =
 const scriptInvalidConstraint =
   new URL("./testdata/dummy_invalid_constraint_plugin.ts", import.meta.url)
     .href;
+const scriptInvalidConstraint2 =
+  new URL("./testdata/dummy_invalid_constraint_plugin2.ts", import.meta.url)
+    .href;
 
 Deno.test("Service", async (t) => {
   const meta: Meta = {
@@ -189,6 +192,48 @@ Deno.test("Service", async (t) => {
     },
   );
 
+  await t.step(
+    "load() loads plugin and emits autocmd events (could not find version)",
+    async () => {
+      const c = stub(console, "warn");
+      const s = stub(host, "call");
+      try {
+        await service.load("dummyFailConstraint2", scriptInvalidConstraint2);
+        const expects = [
+          "********************************************************************************",
+          "Deno module cache issue is detected.",
+          "Execute 'call denops#cache#update(#{reload: v:true})' and restart Vim/Neovim.",
+          "See https://github.com/vim-denops/denops.vim/issues/358 for more detail.",
+          "********************************************************************************",
+        ];
+        assertSpyCalls(c, expects.length);
+        for (let i = 0; i < expects.length; i++) {
+          assertSpyCall(c, i, {
+            args: [expects[i]],
+          });
+        }
+        assertSpyCalls(s, 2);
+        assertSpyCall(s, 0, {
+          args: [
+            "denops#api#cmd",
+            "doautocmd <nomodeline> User DenopsSystemPluginPre:dummyFailConstraint2",
+            {},
+          ],
+        });
+        assertSpyCall(s, 1, {
+          args: [
+            "denops#api#cmd",
+            "doautocmd <nomodeline> User DenopsSystemPluginFail:dummyFailConstraint2",
+            {},
+          ],
+        });
+      } finally {
+        s.restore();
+        c.restore();
+      }
+    },
+  );
+
   await t.step(
     "load() does nothing when the plugin is already loaded",
     async () => {
diff --git a/denops/@denops-private/testdata/dummy_invalid_constraint_plugin2.ts b/denops/@denops-private/testdata/dummy_invalid_constraint_plugin2.ts
new file mode 100644
index 00000000..d0d8c59c
--- /dev/null
+++ b/denops/@denops-private/testdata/dummy_invalid_constraint_plugin2.ts
@@ -0,0 +1,8 @@
+import type { Entrypoint } from "https://deno.land/x/denops_core@v6.1.0/mod.ts";
+
+export const main: Entrypoint = (_denops) => {
+  // Mimic the situation
+  throw new TypeError(
+    "Could not find version of '@std/path' that matches specified version constraint '0.225.2'",
+  );
+};