diff --git a/.gitpod.yml b/.gitpod.yml
new file mode 100644
index 000000000..b03003160
--- /dev/null
+++ b/.gitpod.yml
@@ -0,0 +1,55 @@
+tasks:
+  - init: |
+      npm i &&
+      npm run dx:up &&
+      cp .env.example .env &&
+      set -a; source .env &&
+      export NEXTAUTH_URL="$(gp url 3000)" &&
+      export NEXT_PUBLIC_WEBAPP_URL="$(gp url 3000)" &&
+      export NEXT_PUBLIC_MARKETING_URL="$(gp url 3001)" 
+    command: npm run d
+
+ports:
+  - port: 3000
+    visibility: public
+    onOpen: open-preview
+  - port: 3001
+    visibility: public
+    onOpen: open-preview
+  - port: 9000
+    visibility: public
+    onOpen: ignore
+  - port: 1100
+    visibility: private
+    onOpen: ignore
+  - port: 2500
+    visibility: private
+    onOpen: ignore
+  - port: 54320 
+    visibility: private 
+    onOpen: ignore
+
+
+github:
+  prebuilds:
+    master: true
+    pullRequests: true
+    pullRequestsFromForks: true
+    addCheck: true
+    addComment: true
+    addBadge: true
+
+vscode:
+  extensions:
+    - aaron-bond.better-comments
+    - bradlc.vscode-tailwindcss
+    - dbaeumer.vscode-eslint
+    - esbenp.prettier-vscode
+    - mikestead.dotenv
+    - unifiedjs.vscode-mdx
+    - GitHub.copilot-chat
+    - GitHub.copilot-labs
+    - GitHub.copilot
+    - GitHub.vscode-pull-request-github
+    - Prisma.prisma
+    - VisualStudioExptTeam.vscodeintellicode
diff --git a/apps/web/src/app/(signing)/sign/[token]/signature-field.tsx b/apps/web/src/app/(signing)/sign/[token]/signature-field.tsx
index 020af41c2..01923bd6c 100644
--- a/apps/web/src/app/(signing)/sign/[token]/signature-field.tsx
+++ b/apps/web/src/app/(signing)/sign/[token]/signature-field.tsx
@@ -1,6 +1,6 @@
 'use client';
 
-import { useMemo, useState, useTransition } from 'react';
+import { useEffect, useMemo, useState, useTransition } from 'react';
 
 import { useRouter } from 'next/navigation';
 
@@ -48,6 +48,7 @@ export const SignatureField = ({ field, recipient }: SignatureFieldProps) => {
 
   const [showSignatureModal, setShowSignatureModal] = useState(false);
   const [localSignature, setLocalSignature] = useState<string | null>(null);
+  const [isLocalSignatureSet, setIsLocalSignatureSet] = useState(false);
 
   const state = useMemo<SignatureFieldState>(() => {
     if (!field.inserted) {
@@ -61,9 +62,16 @@ export const SignatureField = ({ field, recipient }: SignatureFieldProps) => {
     return 'signed-text';
   }, [field.inserted, signature?.signatureImageAsBase64]);
 
+  useEffect(() => {
+    if (!showSignatureModal && !isLocalSignatureSet) {
+      setLocalSignature(null);
+    }
+  }, [showSignatureModal, isLocalSignatureSet]);
+
   const onSign = async (source: 'local' | 'provider' = 'provider') => {
     try {
       if (!providedSignature && !localSignature) {
+        setIsLocalSignatureSet(false);
         setShowSignatureModal(true);
         return;
       }
@@ -178,6 +186,7 @@ export const SignatureField = ({ field, recipient }: SignatureFieldProps) => {
                 disabled={!localSignature}
                 onClick={() => {
                   setShowSignatureModal(false);
+                  setIsLocalSignatureSet(true);
                   void onSign('local');
                 }}
               >