diff --git a/packages/cli/commands/project/deploy.js b/packages/cli/commands/project/deploy.js
index 6b969ace9..5dc5c7089 100644
--- a/packages/cli/commands/project/deploy.js
+++ b/packages/cli/commands/project/deploy.js
@@ -87,11 +87,7 @@ exports.handler = async options => {
     if (e.statusCode === 400) {
       logger.error(e.error.message);
     } else {
-      logApiErrorInstance(
-        accountId,
-        e,
-        new ApiErrorContext({ accountId, projectPath })
-      );
+      logApiErrorInstance(e, new ApiErrorContext({ accountId, projectPath }));
     }
   }
 };
diff --git a/packages/cli/commands/project/upload.js b/packages/cli/commands/project/upload.js
index 512ac0428..22220029d 100644
--- a/packages/cli/commands/project/upload.js
+++ b/packages/cli/commands/project/upload.js
@@ -31,6 +31,7 @@ const {
   getProjectConfig,
   validateProjectConfig,
   pollBuildStatus,
+  ensureProjectExists,
 } = require('../../lib/projects');
 
 const loadAndValidateOptions = async options => {
@@ -83,12 +84,13 @@ const uploadProjectFiles = async (accountId, projectName, filePath) => {
       )} project files to ${chalk.bold(accountId)}`,
     });
 
-    logApiErrorInstance(err, {
-      context: new ApiErrorContext({
+    logApiErrorInstance(
+      err,
+      new ApiErrorContext({
         accountId,
         projectName,
-      }),
-    });
+      })
+    );
   }
 };
 
@@ -100,10 +102,14 @@ exports.handler = async options => {
 
   trackCommandUsage('project-upload', { projectPath }, accountId);
 
-  const cwd = projectPath ? path.resolve(getCwd(), projectPath) : getCwd();
-  const projectConfig = await getProjectConfig(cwd);
+  const projectDir = projectPath
+    ? path.resolve(getCwd(), projectPath)
+    : getCwd();
+  const projectConfig = await getProjectConfig(projectDir);
+
+  validateProjectConfig(projectConfig, projectDir);
 
-  validateProjectConfig(projectConfig);
+  await ensureProjectExists(accountId, projectConfig.name);
 
   const tempFile = tmp.fileSync({ postfix: '.zip' });
 
@@ -131,8 +137,10 @@ exports.handler = async options => {
 
   archive.pipe(output);
 
-  archive.directory(path.resolve(cwd, projectConfig.srcDir), false, file =>
-    shouldIgnoreFile(file.name) ? false : file
+  archive.directory(
+    path.resolve(projectDir, projectConfig.srcDir),
+    false,
+    file => (shouldIgnoreFile(file.name) ? false : file)
   );
 
   archive.finalize();
diff --git a/packages/cli/lib/projects.js b/packages/cli/lib/projects.js
index 6d5fb84d7..40889b49a 100644
--- a/packages/cli/lib/projects.js
+++ b/packages/cli/lib/projects.js
@@ -16,7 +16,16 @@ const {
   PROJECT_DEPLOY_STATUS,
   PROJECT_DEPLOY_STATUS_TEXT,
 } = require('@hubspot/cli-lib/lib/constants');
-const { getBuildStatus, getDeployStatus } = require('@hubspot/cli-lib/api/dfs');
+const {
+  getBuildStatus,
+  getDeployStatus,
+  fetchProject,
+  createProject,
+} = require('@hubspot/cli-lib/api/dfs');
+const {
+  logApiErrorInstance,
+  ApiErrorContext,
+} = require('@hubspot/cli-lib/errorHandlers');
 
 const isBuildComplete = build => {
   return (
@@ -88,7 +97,7 @@ const getOrCreateProjectConfig = async projectPath => {
   return projectConfig;
 };
 
-const validateProjectConfig = projectConfig => {
+const validateProjectConfig = (projectConfig, projectDir) => {
   if (!projectConfig) {
     logger.error(
       `Project config not found. Try running 'hs project init' first.`
@@ -103,7 +112,7 @@ const validateProjectConfig = projectConfig => {
     process.exit(1);
   }
 
-  if (!fs.existsSync(projectConfig.srcDir)) {
+  if (!fs.existsSync(path.resolve(projectDir, projectConfig.srcDir))) {
     logger.error(
       `Project source directory '${projectConfig.srcDir}' does not exist.`
     );
@@ -111,6 +120,37 @@ const validateProjectConfig = projectConfig => {
   }
 };
 
+const ensureProjectExists = async (accountId, projectName) => {
+  try {
+    await fetchProject(accountId, projectName);
+  } catch (err) {
+    if (err.statusCode === 404) {
+      const { shouldCreateProject } = await prompt([
+        {
+          name: 'shouldCreateProject',
+          message: `The project ${projectName} does not exist in ${accountId}. Would you like to create it?`,
+          type: 'confirm',
+        },
+      ]);
+
+      if (shouldCreateProject) {
+        try {
+          return createProject(accountId, projectName);
+        } catch (err) {
+          return logApiErrorInstance(err, new ApiErrorContext({ accountId }));
+        }
+      } else {
+        return logger.log(
+          `Your project ${chalk.bold(
+            projectName
+          )} could not be found in ${chalk.bold(accountId)}.`
+        );
+      }
+    }
+    logApiErrorInstance(err, new ApiErrorContext({ accountId }));
+  }
+};
+
 const getProjectDetailUrl = (projectName, accountId) => {
   if (!projectName) return;
 
@@ -335,4 +375,5 @@ module.exports = {
   showWelcomeMessage,
   pollBuildStatus,
   pollDeployStatus,
+  ensureProjectExists,
 };