diff --git a/.env.example b/.env.example
index f21560ca3..c482c128e 100644
--- a/.env.example
+++ b/.env.example
@@ -74,6 +74,8 @@ NEXT_PRIVATE_MAILCHANNELS_DKIM_DOMAIN=
 NEXT_PRIVATE_MAILCHANNELS_DKIM_SELECTOR=
 # OPTIONAL: The private key to use for DKIM signing.
 NEXT_PRIVATE_MAILCHANNELS_DKIM_PRIVATE_KEY=
+# OPTIONAL: Displays the maximum document upload limit to the user in MBs
+NEXT_PUBLIC_DOCUMENT_SIZE_UPLOAD_LIMIT=5
 
 # [[STRIPE]]
 NEXT_PRIVATE_STRIPE_API_KEY=
diff --git a/apps/web/src/app/(dashboard)/documents/upload-document.tsx b/apps/web/src/app/(dashboard)/documents/upload-document.tsx
index 65b95f9ec..444bd1db0 100644
--- a/apps/web/src/app/(dashboard)/documents/upload-document.tsx
+++ b/apps/web/src/app/(dashboard)/documents/upload-document.tsx
@@ -10,6 +10,7 @@ import { useSession } from 'next-auth/react';
 
 import { useLimits } from '@documenso/ee/server-only/limits/provider/client';
 import { useAnalytics } from '@documenso/lib/client-only/hooks/use-analytics';
+import { APP_DOCUMENT_UPLOAD_SIZE_LIMIT } from '@documenso/lib/constants/app';
 import { createDocumentData } from '@documenso/lib/server-only/document-data/create-document-data';
 import { putFile } from '@documenso/lib/universal/upload/put-file';
 import { TRPCClientError } from '@documenso/trpc/client';
@@ -96,6 +97,15 @@ export const UploadDocument = ({ className }: UploadDocumentProps) => {
     }
   };
 
+  const onFileDropRejected = () => {
+    toast({
+      title: 'Your document failed to upload.',
+      description: `File cannot be larger than ${APP_DOCUMENT_UPLOAD_SIZE_LIMIT}MB`,
+      duration: 5000,
+      variant: 'destructive',
+    });
+  };
+
   return (
     <div className={cn('relative', className)}>
       <DocumentDropzone
@@ -103,6 +113,7 @@ export const UploadDocument = ({ className }: UploadDocumentProps) => {
         disabled={remaining.documents === 0 || !session?.user.emailVerified}
         disabledMessage={disabledMessage}
         onDrop={onFileDrop}
+        onDropRejected={onFileDropRejected}
       />
 
       <div className="absolute -bottom-6 right-0">
diff --git a/packages/lib/constants/app.ts b/packages/lib/constants/app.ts
index 827fcef0a..a19d2bb0d 100644
--- a/packages/lib/constants/app.ts
+++ b/packages/lib/constants/app.ts
@@ -6,3 +6,6 @@ export const APP_FOLDER = IS_APP_MARKETING ? 'marketing' : 'web';
 export const APP_BASE_URL = IS_APP_WEB
   ? process.env.NEXT_PUBLIC_WEBAPP_URL
   : process.env.NEXT_PUBLIC_MARKETING_URL;
+
+export const APP_DOCUMENT_UPLOAD_SIZE_LIMIT =
+  Number(process.env.NEXT_PUBLIC_DOCUMENT_SIZE_UPLOAD_LIMIT) || 50;
diff --git a/packages/ui/primitives/document-dropzone.tsx b/packages/ui/primitives/document-dropzone.tsx
index 21337956d..6caf6d040 100644
--- a/packages/ui/primitives/document-dropzone.tsx
+++ b/packages/ui/primitives/document-dropzone.tsx
@@ -5,6 +5,7 @@ import { motion } from 'framer-motion';
 import { Plus } from 'lucide-react';
 import { useDropzone } from 'react-dropzone';
 
+import { APP_DOCUMENT_UPLOAD_SIZE_LIMIT } from '@documenso/lib/constants/app';
 import { megabytesToBytes } from '@documenso/lib/universal/unit-convertions';
 
 import { cn } from '../lib/utils';
@@ -89,6 +90,7 @@ export type DocumentDropzoneProps = {
   disabled?: boolean;
   disabledMessage?: string;
   onDrop?: (_file: File) => void | Promise<void>;
+  onDropRejected?: () => void | Promise<void>;
   type?: 'document' | 'template';
   [key: string]: unknown;
 };
@@ -96,6 +98,7 @@ export type DocumentDropzoneProps = {
 export const DocumentDropzone = ({
   className,
   onDrop,
+  onDropRejected,
   disabled,
   disabledMessage = 'You cannot upload documents at this time.',
   type = 'document',
@@ -112,7 +115,12 @@ export const DocumentDropzone = ({
         void onDrop(acceptedFile);
       }
     },
-    maxSize: megabytesToBytes(50),
+    onDropRejected: () => {
+      if (onDropRejected) {
+        void onDropRejected();
+      }
+    },
+    maxSize: megabytesToBytes(APP_DOCUMENT_UPLOAD_SIZE_LIMIT),
   });
 
   return (
@@ -175,7 +183,7 @@ export const DocumentDropzone = ({
           </p>
 
           <p className="text-muted-foreground/80 mt-1 text-sm">
-            {disabled ? disabledMessage : 'Drag & drop your document here.'}
+            {disabled ? disabledMessage : 'Drag & drop your PDF here.'}
           </p>
         </CardContent>
       </Card>
diff --git a/turbo.json b/turbo.json
index b78d7c9d0..b0a7a0fc6 100644
--- a/turbo.json
+++ b/turbo.json
@@ -45,6 +45,7 @@
     "NEXT_PUBLIC_STRIPE_COMMUNITY_PLAN_MONTHLY_PRICE_ID",
     "NEXT_PUBLIC_STRIPE_FREE_PLAN_ID",
     "NEXT_PUBLIC_DISABLE_SIGNUP",
+    "NEXT_PUBLIC_DOCUMENT_SIZE_UPLOAD_LIMIT",
     "NEXT_PRIVATE_DATABASE_URL",
     "NEXT_PRIVATE_DIRECT_DATABASE_URL",
     "NEXT_PRIVATE_GOOGLE_CLIENT_ID",