diff --git a/packages/ui/lib/calculate-period.ts b/packages/ui/lib/calculate-period.ts
new file mode 100644
index 000000000..ffa9375cc
--- /dev/null
+++ b/packages/ui/lib/calculate-period.ts
@@ -0,0 +1,16 @@
+import { differenceInDays, differenceInMonths, differenceInWeeks } from 'date-fns';
+
+export const calculatePeriod = (expiryDate: Date) => {
+  const now = new Date();
+  const daysDiff = differenceInDays(expiryDate, now);
+  const weeksDiff = differenceInWeeks(expiryDate, now);
+  const monthsDiff = differenceInMonths(expiryDate, now);
+
+  if (monthsDiff > 0) {
+    return { amount: monthsDiff, unit: 'months' as const };
+  } else if (weeksDiff > 0) {
+    return { amount: weeksDiff, unit: 'weeks' as const };
+  } else {
+    return { amount: daysDiff, unit: 'days' as const };
+  }
+};
diff --git a/packages/ui/primitives/document-flow/document-expiry-dialog.tsx b/packages/ui/primitives/document-flow/document-expiry-dialog.tsx
index f797ea0ea..0a752c0b2 100644
--- a/packages/ui/primitives/document-flow/document-expiry-dialog.tsx
+++ b/packages/ui/primitives/document-flow/document-expiry-dialog.tsx
@@ -1,11 +1,13 @@
 'use client';
 
+import { useState } from 'react';
+
 import { useRouter } from 'next/navigation';
 
 import { zodResolver } from '@hookform/resolvers/zod';
 import { Trans, msg } from '@lingui/macro';
 import { useLingui } from '@lingui/react';
-import { format } from 'date-fns';
+import { addDays, addMonths, addWeeks, format } from 'date-fns';
 import { Calendar as CalendarIcon } from 'lucide-react';
 import { useForm } from 'react-hook-form';
 import * as z from 'zod';
@@ -32,17 +34,31 @@ import {
   FormMessage,
 } from '@documenso/ui/primitives/form/form';
 import { Popover, PopoverContent, PopoverTrigger } from '@documenso/ui/primitives/popover';
+import {
+  Select,
+  SelectContent,
+  SelectItem,
+  SelectTrigger,
+  SelectValue,
+} from '@documenso/ui/primitives/select';
+import { Tabs, TabsContent, TabsList, TabsTrigger } from '@documenso/ui/primitives/tabs';
 
+import { calculatePeriod } from '../../lib/calculate-period';
 import { cn } from '../../lib/utils';
 import { useToast } from '../use-toast';
 import type { TAddSignerSchema as Signer } from './add-signers.types';
 
-const formSchema = z.object({
+const dateFormSchema = z.object({
   expiry: z.date({
     required_error: 'Please select an expiry date.',
   }),
 });
 
+const periodFormSchema = z.object({
+  amount: z.number().min(1, 'Please enter a number greater than 0.'),
+  unit: z.enum(['days', 'weeks', 'months']),
+});
+
 type DocumentExpiryDialogProps = {
   open: boolean;
   onOpenChange: (_open: boolean) => void;
@@ -56,21 +72,53 @@ export default function DocumentExpiryDialog({
   signer,
   documentId,
 }: DocumentExpiryDialogProps) {
-  const { toast } = useToast();
-  const router = useRouter();
-
   const { _ } = useLingui();
+  const router = useRouter();
+  const { toast } = useToast();
+  const [activeTab, setActiveTab] = useState<'date' | 'period'>('date');
 
-  const form = useForm<z.infer<typeof formSchema>>({
-    resolver: zodResolver(formSchema),
+  const dateForm = useForm<z.infer<typeof dateFormSchema>>({
+    resolver: zodResolver(dateFormSchema),
     defaultValues: {
       expiry: signer.expiry,
     },
   });
 
+  const periodForm = useForm<z.infer<typeof periodFormSchema>>({
+    resolver: zodResolver(periodFormSchema),
+    defaultValues: signer.expiry
+      ? calculatePeriod(signer.expiry)
+      : {
+          amount: undefined,
+          unit: undefined,
+        },
+  });
+
+  const watchAmount = periodForm.watch('amount');
+  const watchUnit = periodForm.watch('unit');
+
   const { mutateAsync: setSignerExpiry, isLoading } = trpc.recipient.setSignerExpiry.useMutation({
-    onSuccess: () => {
+    onSuccess: ({ expired }) => {
       router.refresh();
+
+      periodForm.reset(
+        expired
+          ? calculatePeriod(expired)
+          : {
+              amount: undefined,
+              unit: undefined,
+            },
+      );
+
+      dateForm.reset(
+        {
+          expiry: expired ?? undefined,
+        },
+        {
+          keepValues: false,
+        },
+      );
+
       toast({
         title: _(msg`Signer Expiry Set`),
         description: _(msg`The expiry date for the signer has been set.`),
@@ -88,7 +136,9 @@ export default function DocumentExpiryDialog({
     },
   });
 
-  const onSetExpiry = async (values: z.infer<typeof formSchema>) => {
+  const onSetExpiry = async (
+    values: z.infer<typeof dateFormSchema> | z.infer<typeof periodFormSchema>,
+  ) => {
     if (!signer.nativeId) {
       return toast({
         title: _(msg`Error`),
@@ -98,11 +148,38 @@ export default function DocumentExpiryDialog({
       });
     }
 
+    let expiryDate: Date;
+
+    if ('expiry' in values) {
+      expiryDate = values.expiry;
+    } else {
+      const now = new Date();
+      switch (values.unit) {
+        case 'days':
+          expiryDate = addDays(now, values.amount);
+          break;
+        case 'weeks':
+          expiryDate = addWeeks(now, values.amount);
+          break;
+        case 'months':
+          expiryDate = addMonths(now, values.amount);
+          break;
+      }
+    }
+
+    console.log('finalll expiry date', expiryDate);
+
     await setSignerExpiry({
       documentId,
       signerId: signer.nativeId,
-      expiry: new Date(values.expiry),
+      expiry: expiryDate,
     });
+
+    // TODO: Implement logic to update expiry when resending document
+    // This should be handled on the server-side when a document is resent
+
+    // TODO: Implement logic to mark recipients as expired
+    // This should be a scheduled task or part of the completion process on the server
   };
 
   return (
@@ -115,58 +192,143 @@ export default function DocumentExpiryDialog({
             to sign the document after this date.
           </DialogDescription>
         </DialogHeader>
-        <Form {...form}>
-          <form onSubmit={form.handleSubmit(onSetExpiry)} className="space-y-8">
-            <FormField
-              control={form.control}
-              name="expiry"
-              render={({ field }) => (
-                <FormItem className="flex flex-col">
-                  <FormLabel>Expiry Date</FormLabel>
-                  <Popover>
-                    <PopoverTrigger asChild>
-                      <FormControl>
-                        <Button
-                          variant={'outline'}
-                          className={cn(
-                            'w-[240px] pl-3 text-left font-normal',
-                            !field.value && 'text-muted-foreground',
-                          )}
-                        >
-                          {field.value ? format(field.value, 'PPP') : <span>Pick a date</span>}
-                          <CalendarIcon className="ml-auto h-4 w-4 opacity-50" />
-                        </Button>
-                      </FormControl>
-                    </PopoverTrigger>
-                    <PopoverContent className="z-[1100] w-auto p-0 " align="start">
-                      <Calendar
-                        mode="single"
-                        selected={field.value}
-                        onSelect={field.onChange}
-                        disabled={(date) => date < new Date() || date < new Date('1900-01-01')}
-                        initialFocus
-                      />
-                    </PopoverContent>
-                  </Popover>
-                  <FormDescription>
-                    The document will expire at 11:59 PM on the selected date.
-                  </FormDescription>
-                  <FormMessage />
-                </FormItem>
-              )}
-            />
-            <DialogFooter>
-              <DialogClose asChild>
-                <Button type="button" variant="secondary">
-                  <Trans>Cancel</Trans>
-                </Button>
-              </DialogClose>
-              <Button type="submit" loading={isLoading}>
-                <Trans>Save Changes</Trans>
-              </Button>
-            </DialogFooter>
-          </form>
-        </Form>
+        <Tabs
+          value={activeTab}
+          onValueChange={(value) => {
+            // eslint-disable-next-line @typescript-eslint/consistent-type-assertions
+            return setActiveTab(value as 'date' | 'period');
+          }}
+        >
+          <TabsList className="grid w-full grid-cols-2">
+            <TabsTrigger value="date">Specific Date</TabsTrigger>
+            <TabsTrigger value="period">Time Period</TabsTrigger>
+          </TabsList>
+          <TabsContent value="date">
+            <Form {...dateForm}>
+              <form onSubmit={dateForm.handleSubmit(onSetExpiry)} className="space-y-8">
+                <FormField
+                  control={dateForm.control}
+                  name="expiry"
+                  render={({ field }) => (
+                    <FormItem className="flex flex-col">
+                      <FormLabel>Expiry Date</FormLabel>
+                      <Popover>
+                        <PopoverTrigger asChild>
+                          <FormControl>
+                            <Button
+                              variant={'outline'}
+                              className={cn(
+                                'w-[240px] pl-3 text-left font-normal',
+                                !field.value && 'text-muted-foreground',
+                              )}
+                            >
+                              {field.value ? format(field.value, 'PPP') : <span>Pick a date</span>}
+                              <CalendarIcon className="ml-auto h-4 w-4 opacity-50" />
+                            </Button>
+                          </FormControl>
+                        </PopoverTrigger>
+                        <PopoverContent className="z-[1100] w-auto p-0" align="start">
+                          <Calendar
+                            mode="single"
+                            selected={field.value}
+                            onSelect={field.onChange}
+                            disabled={(date) => date < new Date() || date < new Date('1900-01-01')}
+                            initialFocus
+                          />
+                        </PopoverContent>
+                      </Popover>
+                      <FormDescription>
+                        The document will expire at 11:59 PM on the selected date.
+                      </FormDescription>
+                      <FormMessage />
+                    </FormItem>
+                  )}
+                />
+                <DialogFooter>
+                  <DialogClose asChild>
+                    <Button type="button" variant="secondary">
+                      <Trans>Cancel</Trans>
+                    </Button>
+                  </DialogClose>
+                  <Button type="submit" loading={isLoading}>
+                    <Trans>Save Changes</Trans>
+                  </Button>
+                </DialogFooter>
+              </form>
+            </Form>
+          </TabsContent>
+          <TabsContent value="period">
+            <Form {...periodForm}>
+              <form onSubmit={periodForm.handleSubmit(onSetExpiry)} className="space-y-8">
+                <div className="flex space-x-4">
+                  <FormField
+                    control={periodForm.control}
+                    name="amount"
+                    render={({ field }) => (
+                      <FormItem className="flex-1">
+                        <FormLabel>Amount</FormLabel>
+                        <FormControl>
+                          <Select
+                            onValueChange={(value) => field.onChange(parseInt(value, 10))}
+                            value={watchAmount?.toString()}
+                          >
+                            <SelectTrigger>
+                              <SelectValue placeholder="Select amount" />
+                            </SelectTrigger>
+                            <SelectContent>
+                              {[1, 2, 3, 4, 5, 6, 7, 8, 9, 10].map((num) => (
+                                <SelectItem key={num} value={num.toString()}>
+                                  {num}
+                                </SelectItem>
+                              ))}
+                            </SelectContent>
+                          </Select>
+                        </FormControl>
+                        <FormMessage />
+                      </FormItem>
+                    )}
+                  />
+                  <FormField
+                    control={periodForm.control}
+                    name="unit"
+                    render={({ field }) => (
+                      <FormItem className="flex-1">
+                        <FormLabel>Unit</FormLabel>
+                        <FormControl>
+                          <Select onValueChange={field.onChange} value={watchUnit}>
+                            {' '}
+                            <SelectTrigger>
+                              <SelectValue placeholder="Select unit" />
+                            </SelectTrigger>
+                            <SelectContent>
+                              <SelectItem value="days">Days</SelectItem>
+                              <SelectItem value="weeks">Weeks</SelectItem>
+                              <SelectItem value="months">Months</SelectItem>
+                            </SelectContent>
+                          </Select>
+                        </FormControl>
+                        <FormMessage />
+                      </FormItem>
+                    )}
+                  />
+                </div>
+                <FormDescription>
+                  The document will expire after the selected time period from now.
+                </FormDescription>
+                <DialogFooter>
+                  <DialogClose asChild>
+                    <Button type="button" variant="secondary">
+                      <Trans>Cancel</Trans>
+                    </Button>
+                  </DialogClose>
+                  <Button type="submit" loading={isLoading}>
+                    <Trans>Save Changes</Trans>
+                  </Button>
+                </DialogFooter>
+              </form>
+            </Form>
+          </TabsContent>
+        </Tabs>
       </DialogContent>
     </Dialog>
   );