diff --git a/.changeset/serious-chicken-sing.md b/.changeset/serious-chicken-sing.md
new file mode 100644
index 0000000..45b5552
--- /dev/null
+++ b/.changeset/serious-chicken-sing.md
@@ -0,0 +1,5 @@
+---
+'@clarigen/cli': patch
+---
+
+Fixes `clarigen --watch` by generating types automatically, and properly reloading the session when files change.
diff --git a/packages/cli/src/clarinet-sdk.ts b/packages/cli/src/clarinet-sdk.ts
index 90cca6d..ac2edc6 100644
--- a/packages/cli/src/clarinet-sdk.ts
+++ b/packages/cli/src/clarinet-sdk.ts
@@ -13,7 +13,7 @@ import { mapVariables } from './files/variables';
 import { SessionContract, SessionWithVariables } from './session';
 
 export async function getSession(config: Config): Promise<SessionWithVariables> {
-  const simnet = await initSimnet(config.clarinetFile());
+  const simnet = await initSimnet(config.clarinetFile(), true);
   const interfaces = simnet.getContractsInterfaces();
   const accounts = simnet.getAccounts();
 
diff --git a/packages/cli/src/commands/default-command.ts b/packages/cli/src/commands/default-command.ts
index c11757e..78141ea 100644
--- a/packages/cli/src/commands/default-command.ts
+++ b/packages/cli/src/commands/default-command.ts
@@ -28,9 +28,11 @@ export async function generate(config: Config) {
 
 export async function watch(config: Config, cwd?: string) {
   // const ora = await import('ora');
-  return new Promise((resolve, reject) => {
+  return new Promise(async (resolve, reject) => {
     const clarinetFolder = dirname(config.clarinetFile());
     const contractsFolder = join(clarinetFolder, '/contracts/**/*.clar');
+    // First, generate the types
+    await generate(config);
     // const watchCwd = cwd || process.cwd();
     const relativeFolder = relative(cwd || process.cwd(), contractsFolder);
     logger.info(`Watching for changes in ${relativeFolder}`);