diff --git a/.changeset/cli-dev-without-project.md b/.changeset/cli-dev-without-project.md
new file mode 100644
index 0000000000..4e5b74a7f6
--- /dev/null
+++ b/.changeset/cli-dev-without-project.md
@@ -0,0 +1,5 @@
+---
+"trigger.dev": patch
+---
+
+Running a CLI command like `dev`, `deploy`, `preview`, or `update` before initializing a project no longer crashes with a raw `Cannot find matching package.json` stack trace. The CLI now detects the missing project and points you to `npx trigger.dev@latest init` instead.
diff --git a/packages/cli-v3/src/commands/update.ts b/packages/cli-v3/src/commands/update.ts
index f94718213f..b7df5837f2 100644
--- a/packages/cli-v3/src/commands/update.ts
+++ b/packages/cli-v3/src/commands/update.ts
@@ -66,13 +66,35 @@ export async function updateTriggerPackages(
 
   const projectPath = resolve(process.cwd(), dir);
 
-  const { packageJson, readonlyPackageJson, packageJsonPath } = await getPackageJson(projectPath);
+  let packageJsonResult: Awaited<ReturnType<typeof getPackageJson>> | undefined;
+
+  try {
+    packageJsonResult = await getPackageJson(projectPath);
+  } catch (error) {
+    // resolvePackageJSON throws when there's no package.json in projectPath or any parent
+    // directory — usually because the command ran before the project was set up. Don't crash
+    // with a raw stack trace; fall through to the actionable guidance below.
+    logger.debug("Failed to resolve package.json for update check", { projectPath, error });
+  }
+
+  if (!packageJsonResult?.packageJson) {
+    prettyError(
+      "No package.json found",
+      `Couldn't find a package.json in ${projectPath} or any parent directory.`,
+      "Run `npx trigger.dev@latest init` to set up your project, then try again."
+    );
+
+    // When embedded in another command (e.g. `dev`), there's nothing to run without a project,
+    // so stop here with a clean exit instead of letting the caller fail again downstream.
+    if (embedded) {
+      process.exit(1);
+    }
 
-  if (!packageJson) {
-    log.error("Failed to load package.json. Try to re-run with `-l debug` to see what's going on.");
     return false;
   }
 
+  const { packageJson, readonlyPackageJson, packageJsonPath } = packageJsonResult;
+
   const newCliVersion = await updateCheck();
 
   if (newCliVersion && !cliVersion.startsWith("0.0.0")) {
diff --git a/packages/cli-v3/src/config.ts b/packages/cli-v3/src/config.ts
index af5623e017..1421cafe06 100644
--- a/packages/cli-v3/src/config.ts
+++ b/packages/cli-v3/src/config.ts
@@ -152,18 +152,9 @@ async function resolveConfig(
   overrides?: Partial<TriggerConfig>,
   warn = true
 ): Promise<ResolvedConfig> {
-  const packageJsonPath = await resolvePackageJSON(cwd);
-  const tsconfigPath = await safeResolveTsConfig(cwd);
-  const lockfilePath = await resolveLockfile(cwd);
-  const workspaceDir = await findWorkspaceDir(cwd);
-
-  const workingDir = result.configFile
-    ? dirname(result.configFile)
-    : packageJsonPath
-    ? dirname(packageJsonPath)
-    : cwd;
-
-  // `trigger.config` is the fallback value set by c12
+  // `trigger.config` is the fallback value set by c12. Bail out with actionable guidance before
+  // touching the filesystem: the pkg-types resolvers below throw raw errors when run outside a
+  // project (e.g. `dev` before `init`), which would mask this message.
   const missingConfigFile = !result.configFile || result.configFile === "trigger.config";
 
   if (missingConfigFile) {
@@ -178,6 +169,17 @@ async function resolveConfig(
     );
   }
 
+  const packageJsonPath = await resolvePackageJSON(cwd);
+  const tsconfigPath = await safeResolveTsConfig(cwd);
+  const lockfilePath = await resolveLockfile(cwd);
+  const workspaceDir = await findWorkspaceDir(cwd);
+
+  const workingDir = result.configFile
+    ? dirname(result.configFile)
+    : packageJsonPath
+    ? dirname(packageJsonPath)
+    : cwd;
+
   const config =
     "config" in result.config ? (result.config.config as TriggerConfig) : result.config;