diff --git a/packages/cdktf-cli/bin/cmds/ui/models/terraform-cloud.ts b/packages/cdktf-cli/bin/cmds/ui/models/terraform-cloud.ts
index 958aa22783..6f795f6e93 100644
--- a/packages/cdktf-cli/bin/cmds/ui/models/terraform-cloud.ts
+++ b/packages/cdktf-cli/bin/cmds/ui/models/terraform-cloud.ts
@@ -7,6 +7,7 @@ import { TerraformJsonConfigBackendRemote } from '../terraform-json'
 import * as TerraformCloudClient from '@skorfmann/terraform-cloud'
 import archiver from 'archiver';
 import { WritableStreamBuffer } from 'stream-buffers';
+import { logger } from '../../../../lib/logging';
 
 export class TerraformCloudPlan implements TerraformPlan {
   constructor(public readonly planFile: string, public readonly plan: { [key: string]: any }, public readonly url: string) { }
@@ -145,6 +146,9 @@ export class TerraformCloud implements Terraform {
     if (!zipBuffer) throw new Error("Couldn't upload directory to Terraform Cloud");
 
     await this.client.ConfigurationVersion.upload(version.attributes.uploadUrl, zipBuffer)
+
+    // we might get an HTTP 422 error if we don't wait for the processing and try to run too early. see #647
+    await this.waitForConfigurationVersionToBeReady();
   }
 
   @BeautifyErrors
@@ -279,4 +283,39 @@ export class TerraformCloud implements Terraform {
       throw e;
     }
   }
+
+  private async isConfigurationVersionReady(): Promise<boolean> {
+    if (!this.configurationVersionId) throw new Error('No ConfigurationVersionId known. Cannot wait for ConfigurationVersion to become ready');
+    const configVersion = await this.client.ConfigurationVersion.show(this.configurationVersionId);
+    const { status } = configVersion.attributes;
+    switch (status) {
+      case 'uploaded': return true;
+      case 'errored': {
+        const { error, errorMessage } = configVersion.attributes;
+        logger.error(`ConfigurationVersion in Terraform Cloud has status "${status}". Returned config version was ${JSON.stringify(configVersion)}`);
+        throw new Error(`Terraform Cloud ConfigurationVersion ${this.configurationVersionId} has status "errored" ${JSON.stringify({ error, errorMessage })}`);
+      }
+      case 'pending': // fallthrough
+      default:
+        logger.debug(`ConfigurationVersion in Terraform Cloud not considered ready with status "${status}".`)
+        return false;
+    }
+  }
+
+  private async waitForConfigurationVersionToBeReady(timeoutMs = 60_000): Promise<void> {
+    logger.debug('waiting for Configuration Version to be ready in Terraform Cloud');
+    let timeoutReached = false;
+    const ready = async () => {
+      while (!(await this.isConfigurationVersionReady() && !timeoutReached)) {
+        await wait(1000);
+      }
+    };
+    const timeout = async () => {
+      await wait(timeoutMs);
+      timeoutReached = true;
+      throw new Error(`Waiting for Terraform Cloud ConfigurationVersion to become ready timed out (timeout was ${timeoutMs}ms)`);
+    };
+    await Promise.race([ready(), timeout()]);
+    logger.debug('Configuration Version is ready in Terraform Cloud');
+  }
 }
diff --git a/packages/cdktf-cli/package.json b/packages/cdktf-cli/package.json
index 86968ab783..dc7062b088 100644
--- a/packages/cdktf-cli/package.json
+++ b/packages/cdktf-cli/package.json
@@ -29,7 +29,7 @@
   "dependencies": {
     "@cdktf/hcl2json": "0.0.0",
     "@skorfmann/ink-confirm-input": "^3.0.0",
-    "@skorfmann/terraform-cloud": "^1.9.1",
+    "@skorfmann/terraform-cloud": "^1.10.0",
     "@types/node": "^14.0.26",
     "archiver": "^5.1.0",
     "cdktf": "0.0.0",
diff --git a/yarn.lock b/yarn.lock
index 00cb595aea..ea302a618b 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -1406,6 +1406,14 @@
     prop-types "^15.5.10"
     yn "^3.1.1"
 
+"@skorfmann/terraform-cloud@^1.10.0":
+  version "1.10.0"
+  resolved "https://registry.yarnpkg.com/@skorfmann/terraform-cloud/-/terraform-cloud-1.10.0.tgz#cba669213dacf92aa1a80c8e8d112f0b5e422cc9"
+  integrity sha512-Yd5WWmmUjFYBpQpsAnAntwQMerilNRpHILNPA7x0EkwHhf+5KTSKYZwzYL/bOY1QfGJX6DTnOSHXIRStHZDUgg==
+  dependencies:
+    axios "^0.21.1"
+    camelcase-keys "^6.2.2"
+
 "@skorfmann/terraform-cloud@^1.9.1":
   version "1.9.1"
   resolved "https://registry.yarnpkg.com/@skorfmann/terraform-cloud/-/terraform-cloud-1.9.1.tgz#6fbdf6846efd6fdeb3405126cc91cd7d5c846eff"