diff --git a/src/tests/update-cmd-diagnostics.test.ts b/src/tests/update-cmd-diagnostics.test.ts
new file mode 100644
index 000000000..71fff7b36
--- /dev/null
+++ b/src/tests/update-cmd-diagnostics.test.ts
@@ -0,0 +1,27 @@
+/**
+ * Regression test for #3445: gsd update must print both current and latest
+ * versions for diagnostics, and bypass npm cache.
+ */
+import { test } from "node:test";
+import assert from "node:assert/strict";
+import { readFileSync } from "node:fs";
+import { join, dirname } from "node:path";
+import { fileURLToPath } from "node:url";
+
+const __dirname = dirname(fileURLToPath(import.meta.url));
+
+test("update-cmd prints latest version before comparison (#3445)", () => {
+  const src = readFileSync(join(__dirname, "..", "update-cmd.ts"), "utf-8");
+  const latestPrintIdx = src.indexOf("Latest version:");
+  const comparisonIdx = src.indexOf("compareSemver(latest, current)");
+  assert.ok(latestPrintIdx !== -1, "Must print latest version");
+  assert.ok(latestPrintIdx < comparisonIdx, "Must print latest BEFORE comparison");
+});
+
+test("update-cmd bypasses npm cache (#3445)", () => {
+  const src = readFileSync(join(__dirname, "..", "update-cmd.ts"), "utf-8");
+  assert.ok(
+    src.includes("npm_config_cache"),
+    "Must clear npm cache env to bypass stale registry data",
+  );
+});
diff --git a/src/update-cmd.ts b/src/update-cmd.ts
index ac16a8209..9534fd9f6 100644
--- a/src/update-cmd.ts
+++ b/src/update-cmd.ts
@@ -14,18 +14,21 @@ export async function runUpdate(): Promise<void> {
   process.stdout.write(`${dim}Current version:${reset} v${current}\n`)
   process.stdout.write(`${dim}Checking npm registry...${reset}\n`)
 
-  // Fetch latest version
+  // Fetch latest version — bypass npm client cache to avoid stale results (#3445)
   let latest: string
   try {
-    latest = execSync(`npm view ${NPM_PACKAGE} version`, {
+    latest = execSync(`npm view ${NPM_PACKAGE} version --fetch-retry-mintimeout=3000`, {
       encoding: 'utf-8',
       stdio: ['ignore', 'pipe', 'ignore'],
+      env: { ...process.env, npm_config_cache: '' },
     }).trim()
   } catch {
     process.stderr.write(`${yellow}Failed to reach npm registry.${reset}\n`)
     process.exit(1)
   }
 
+  process.stdout.write(`${dim}Latest version:${reset}  v${latest}\n`)
+
   if (compareSemver(latest, current) <= 0) {
     process.stdout.write(`${green}Already up to date.${reset}\n`)
     return