diff --git a/apps/web/src/components/forms/send-confirmation-email.tsx b/apps/web/src/components/forms/send-confirmation-email.tsx
index ee073d063..33247bf9f 100644
--- a/apps/web/src/components/forms/send-confirmation-email.tsx
+++ b/apps/web/src/components/forms/send-confirmation-email.tsx
@@ -13,6 +13,7 @@ import {
   FormField,
   FormItem,
   FormLabel,
+  FormMessage,
 } from '@documenso/ui/primitives/form/form';
 import { Input } from '@documenso/ui/primitives/input';
 import { useToast } from '@documenso/ui/primitives/use-toast';
@@ -63,31 +64,32 @@ export const SendConfirmationEmailForm = ({ className }: SendConfirmationEmailFo
   };
 
   return (
-    <div>
-      <Form {...form}>
-        <form
-          className={cn('mt-6 flex w-full flex-col gap-y-4', className)}
-          onSubmit={form.handleSubmit(onFormSubmit)}
-        >
-          <fieldset className="flex w-full flex-col gap-y-4" disabled={isSubmitting}>
-            <FormField
-              control={form.control}
-              name="email"
-              render={({ field }) => (
-                <FormItem>
-                  <FormLabel>Email address</FormLabel>
-                  <FormControl>
-                    <Input type="email" {...field} />
-                  </FormControl>
-                </FormItem>
-              )}
-            />
-          </fieldset>
-          <Button size="lg" type="submit" disabled={isSubmitting}>
+    <Form {...form}>
+      <form
+        className={cn('mt-6 flex w-full flex-col gap-y-4', className)}
+        onSubmit={form.handleSubmit(onFormSubmit)}
+      >
+        <fieldset className="flex w-full flex-col gap-y-4" disabled={isSubmitting}>
+          <FormField
+            control={form.control}
+            name="email"
+            render={({ field }) => (
+              <FormItem>
+                <FormLabel>Email address</FormLabel>
+                <FormControl>
+                  <Input type="email" {...field} />
+                </FormControl>
+              </FormItem>
+            )}
+          />
+
+          <FormMessage />
+
+          <Button size="lg" type="submit" disabled={isSubmitting} loading={isSubmitting}>
             Send confirmation email
           </Button>
-        </form>
-      </Form>
-    </div>
+        </fieldset>
+      </form>
+    </Form>
   );
 };
diff --git a/packages/lib/next-auth/auth-options.ts b/packages/lib/next-auth/auth-options.ts
index d28506ca3..723b9cd7b 100644
--- a/packages/lib/next-auth/auth-options.ts
+++ b/packages/lib/next-auth/auth-options.ts
@@ -13,6 +13,7 @@ import { IdentityProvider, UserSecurityAuditLogType } from '@documenso/prisma/cl
 
 import { isTwoFactorAuthenticationEnabled } from '../server-only/2fa/is-2fa-availble';
 import { validateTwoFactorAuthentication } from '../server-only/2fa/validate-2fa';
+import { getLastVerificationToken } from '../server-only/user/get-last-verification-token';
 import { getUserByEmail } from '../server-only/user/get-user-by-email';
 import { sendConfirmationToken } from '../server-only/user/send-confirmation-token';
 import { extractNextAuthRequestMetadata } from '../universal/extract-request-metadata';
@@ -92,12 +93,19 @@ export const NEXT_AUTH_OPTIONS: AuthOptions = {
         }
 
         if (!user.emailVerified) {
-          const totalUserVerificationTokens = user.VerificationToken.length;
-          const lastUserVerificationToken = user.VerificationToken[totalUserVerificationTokens - 1];
+          const [lastUserVerificationToken] = await getLastVerificationToken({ userId: user.id });
+
+          if (!lastUserVerificationToken) {
+            await sendConfirmationToken({ email });
+            throw new Error(ErrorCode.UNVERIFIED_EMAIL);
+          }
+
           const expiredToken =
             DateTime.fromJSDate(lastUserVerificationToken.expires) <= DateTime.now();
+          const lastSentToken = DateTime.fromJSDate(lastUserVerificationToken.createdAt);
+          const sentWithinLastHour = DateTime.now().minus({ hours: 1 }) <= lastSentToken;
 
-          if (totalUserVerificationTokens < 1 || expiredToken) {
+          if (expiredToken || !sentWithinLastHour) {
             await sendConfirmationToken({ email });
           }
 
diff --git a/packages/lib/server-only/user/get-last-verification-token.ts b/packages/lib/server-only/user/get-last-verification-token.ts
new file mode 100644
index 000000000..279a1fcfd
--- /dev/null
+++ b/packages/lib/server-only/user/get-last-verification-token.ts
@@ -0,0 +1,27 @@
+import { prisma } from '@documenso/prisma';
+
+export interface GetLastVerificationTokenOptions {
+  userId: number;
+}
+
+export const getLastVerificationToken = async ({ userId }: GetLastVerificationTokenOptions) => {
+  const user = await prisma.user.findFirstOrThrow({
+    where: {
+      id: userId,
+    },
+    include: {
+      VerificationToken: {
+        select: {
+          expires: true,
+          createdAt: true,
+        },
+        orderBy: {
+          createdAt: 'desc',
+        },
+        take: 1,
+      },
+    },
+  });
+
+  return user.VerificationToken;
+};
diff --git a/packages/lib/server-only/user/get-user-by-email.ts b/packages/lib/server-only/user/get-user-by-email.ts
index 8c61202a2..0a2ef8d16 100644
--- a/packages/lib/server-only/user/get-user-by-email.ts
+++ b/packages/lib/server-only/user/get-user-by-email.ts
@@ -9,8 +9,5 @@ export const getUserByEmail = async ({ email }: GetUserByEmailOptions) => {
     where: {
       email: email.toLowerCase(),
     },
-    include: {
-      VerificationToken: true,
-    },
   });
 };