diff --git a/apps/web/src/app/(dashboard)/documents/_action-items/resend-document.tsx b/apps/web/src/app/(dashboard)/documents/_action-items/resend-document.tsx
index 54bc20b42..f24c38c72 100644
--- a/apps/web/src/app/(dashboard)/documents/_action-items/resend-document.tsx
+++ b/apps/web/src/app/(dashboard)/documents/_action-items/resend-document.tsx
@@ -177,12 +177,7 @@ export const ResendDocumentActionItem = ({
         <DialogFooter>
           <div className="flex w-full flex-1 flex-nowrap gap-4">
             <DialogClose asChild>
-              <Button
-                type="button"
-                className="dark:bg-muted dark:hover:bg-muted/80 flex-1  bg-black/5 hover:bg-black/10"
-                variant="secondary"
-                disabled={isSubmitting}
-              >
+              <Button type="button" className="flex-1" variant="secondary" disabled={isSubmitting}>
                 <Trans>Cancel</Trans>
               </Button>
             </DialogClose>
diff --git a/packages/ui/primitives/calendar.tsx b/packages/ui/primitives/calendar.tsx
index 0c0110441..f4c85f61f 100644
--- a/packages/ui/primitives/calendar.tsx
+++ b/packages/ui/primitives/calendar.tsx
@@ -29,17 +29,25 @@ function Calendar({ className, classNames, showOutsideDays = true, ...props }: C
         nav_button_next: 'absolute right-1',
         table: 'w-full border-collapse space-y-1',
         head_row: 'flex',
-        head_cell: 'text-muted-foreground rounded-md w-9 font-normal text-[0.8rem]',
+        head_cell: 'text-muted-foreground rounded-md w-8 font-normal text-[0.8rem]',
         row: 'flex w-full mt-2',
-        cell: 'text-center text-sm p-0 relative [&:has([aria-selected])]:bg-accent first:[&:has([aria-selected])]:rounded-l-md last:[&:has([aria-selected])]:rounded-r-md focus-within:relative focus-within:z-20',
+        cell: cn(
+          'relative p-0 text-center text-sm focus-within:relative focus-within:z-20 [&:has([aria-selected])]:bg-accent [&:has([aria-selected].day-outside)]:bg-accent/50 [&:has([aria-selected].day-range-end)]:rounded-r-md',
+          props.mode === 'range'
+            ? '[&:has(>.day-range-end)]:rounded-r-md [&:has(>.day-range-start)]:rounded-l-md first:[&:has([aria-selected])]:rounded-l-md last:[&:has([aria-selected])]:rounded-r-md'
+            : '[&:has([aria-selected])]:rounded-md',
+        ),
         day: cn(
           buttonVariants({ variant: 'ghost' }),
-          'h-9 w-9 p-0 font-normal aria-selected:opacity-100',
+          'h-8 w-8 p-0 font-normal aria-selected:opacity-100',
         ),
+        day_range_start: 'day-range-start',
+        day_range_end: 'day-range-end',
         day_selected:
           'bg-primary text-primary-foreground hover:bg-primary hover:text-primary-foreground focus:bg-primary focus:text-primary-foreground',
         day_today: 'bg-accent text-accent-foreground',
-        day_outside: 'text-muted-foreground opacity-50',
+        day_outside:
+          'day-outside text-muted-foreground aria-selected:bg-accent/50 aria-selected:text-muted-foreground',
         day_disabled: 'text-muted-foreground opacity-50',
         day_range_middle: 'aria-selected:bg-accent aria-selected:text-accent-foreground',
         day_hidden: 'invisible',
diff --git a/packages/ui/primitives/dialog.tsx b/packages/ui/primitives/dialog.tsx
index 0b607aaf8..e3b044633 100644
--- a/packages/ui/primitives/dialog.tsx
+++ b/packages/ui/primitives/dialog.tsx
@@ -135,13 +135,13 @@ DialogDescription.displayName = DialogPrimitive.Description.displayName;
 
 export {
   Dialog,
-  DialogTrigger,
-  DialogContent,
-  DialogHeader,
-  DialogFooter,
-  DialogOverlay,
-  DialogTitle,
-  DialogDescription,
-  DialogPortal,
   DialogClose,
+  DialogContent,
+  DialogDescription,
+  DialogFooter,
+  DialogHeader,
+  DialogOverlay,
+  DialogPortal,
+  DialogTitle,
+  DialogTrigger,
 };
diff --git a/packages/ui/primitives/document-flow/add-signers.tsx b/packages/ui/primitives/document-flow/add-signers.tsx
index 5e543385e..7b30d91a2 100644
--- a/packages/ui/primitives/document-flow/add-signers.tsx
+++ b/packages/ui/primitives/document-flow/add-signers.tsx
@@ -8,7 +8,7 @@ import { zodResolver } from '@hookform/resolvers/zod';
 import { Trans, msg } from '@lingui/macro';
 import { useLingui } from '@lingui/react';
 import { motion } from 'framer-motion';
-import { GripVerticalIcon, Plus, Trash } from 'lucide-react';
+import { GripVerticalIcon, Plus } from 'lucide-react';
 import { useSession } from 'next-auth/react';
 import { useFieldArray, useForm } from 'react-hook-form';
 import { prop, sortBy } from 'remeda';
@@ -41,6 +41,7 @@ import {
   DocumentFlowFormContainerStep,
 } from './document-flow-root';
 import { ShowFieldItem } from './show-field-item';
+import { SignerActionDropdown } from './signer-action-dropdown';
 import type { DocumentFlowStep } from './types';
 
 export type AddSignersFormProps = {
@@ -628,24 +629,18 @@ export const AddSignersFormPartial = ({
                                   )}
                                 />
 
-                                <button
-                                  type="button"
-                                  className={cn(
-                                    'mt-auto inline-flex h-10 w-10 items-center justify-center hover:opacity-80 disabled:cursor-not-allowed disabled:opacity-50',
-                                    {
-                                      'mb-6': form.formState.errors.signers?.[index],
-                                    },
-                                  )}
-                                  disabled={
+                                <SignerActionDropdown
+                                  className={cn({
+                                    'mb-6': form.formState.errors.signers?.[index],
+                                  })}
+                                  onDelete={() => onRemoveSigner(index)}
+                                  deleteDisabled={
                                     snapshot.isDragging ||
                                     isSubmitting ||
                                     !canRecipientBeModified(signer.nativeId) ||
                                     signers.length === 1
                                   }
-                                  onClick={() => onRemoveSigner(index)}
-                                >
-                                  <Trash className="h-4 w-4" />
-                                </button>
+                                />
                               </div>
                             </motion.fieldset>
                           </div>
diff --git a/packages/ui/primitives/document-flow/document-expiry-dialog.tsx b/packages/ui/primitives/document-flow/document-expiry-dialog.tsx
new file mode 100644
index 000000000..73d1e7402
--- /dev/null
+++ b/packages/ui/primitives/document-flow/document-expiry-dialog.tsx
@@ -0,0 +1,140 @@
+'use client';
+
+import { zodResolver } from '@hookform/resolvers/zod';
+import { Trans } from '@lingui/macro';
+import { format } from 'date-fns';
+import { Calendar as CalendarIcon } from 'lucide-react';
+import { useForm } from 'react-hook-form';
+import * as z from 'zod';
+
+import { Button } from '@documenso/ui/primitives/button';
+import { Calendar } from '@documenso/ui/primitives/calendar';
+import {
+  Dialog,
+  DialogClose,
+  DialogContent,
+  DialogDescription,
+  DialogFooter,
+  DialogHeader,
+  DialogTitle,
+} from '@documenso/ui/primitives/dialog';
+import {
+  Form,
+  FormControl,
+  FormDescription,
+  FormField,
+  FormItem,
+  FormLabel,
+  FormMessage,
+} from '@documenso/ui/primitives/form/form';
+import { Popover, PopoverContent, PopoverTrigger } from '@documenso/ui/primitives/popover';
+
+import { cn } from '../../lib/utils';
+
+const formSchema = z.object({
+  expiryDate: z.date({
+    required_error: 'Please select an expiry date.',
+  }),
+});
+
+type DocumentExpiryDialogProps = {
+  open: boolean;
+  onOpenChange: (_open: boolean) => void;
+};
+
+export default function DocumentExpiryDialog({ open, onOpenChange }: DocumentExpiryDialogProps) {
+  const form = useForm<z.infer<typeof formSchema>>({
+    resolver: zodResolver(formSchema),
+  });
+
+  // const { mutateAsync: moveDocument, isLoading } = trpc.document.moveDocumentToTeam.useMutation({
+  //   onSuccess: () => {
+  //     router.refresh();
+  //     toast({
+  //       title: _(msg`Document moved`),
+  //       description: _(msg`The document has been successfully moved to the selected team.`),
+  //       duration: 5000,
+  //     });
+  //     onOpenChange(false);
+  //   },
+  //   onError: (error) => {
+  //     toast({
+  //       title: _(msg`Error`),
+  //       description: error.message || _(msg`An error occurred while moving the document.`),
+  //       variant: 'destructive',
+  //       duration: 7500,
+  //     });
+  //   },
+  // });
+
+  function onSubmit(values: z.infer<typeof formSchema>) {
+    console.log(values);
+    onOpenChange(false);
+  }
+
+  return (
+    <Dialog open={open} onOpenChange={onOpenChange}>
+      <DialogContent className="sm:max-w-[450px]">
+        <DialogHeader>
+          <DialogTitle>Set Document Expiry</DialogTitle>
+          <DialogDescription>
+            Set the expiry date for the document signing recipient. The recipient will not be able
+            to sign the document after this date.
+          </DialogDescription>
+        </DialogHeader>
+        <Form {...form}>
+          <form onSubmit={form.handleSubmit(onSubmit)} className="space-y-8">
+            <FormField
+              control={form.control}
+              name="expiryDate"
+              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">
+                <Trans>Save Changes</Trans>
+              </Button>
+            </DialogFooter>
+          </form>
+        </Form>
+      </DialogContent>
+    </Dialog>
+  );
+}
diff --git a/packages/ui/primitives/document-flow/show-field-item.tsx b/packages/ui/primitives/document-flow/show-field-item.tsx
index ced978e7c..acffa9ddd 100644
--- a/packages/ui/primitives/document-flow/show-field-item.tsx
+++ b/packages/ui/primitives/document-flow/show-field-item.tsx
@@ -36,7 +36,7 @@ export const ShowFieldItem = ({ field, recipients }: ShowFieldItemProps) => {
 
   return createPortal(
     <div
-      className={cn('pointer-events-none absolute z-10 opacity-75')}
+      className={cn('pointer-events-none absolute opacity-75')}
       style={{
         top: `${coords.y}px`,
         left: `${coords.x}px`,
diff --git a/packages/ui/primitives/document-flow/signer-action-dropdown.tsx b/packages/ui/primitives/document-flow/signer-action-dropdown.tsx
new file mode 100644
index 000000000..73ecb262b
--- /dev/null
+++ b/packages/ui/primitives/document-flow/signer-action-dropdown.tsx
@@ -0,0 +1,51 @@
+'use client';
+
+import { useState } from 'react';
+
+import { MoreHorizontal, Timer, Trash } from 'lucide-react';
+
+import {
+  DropdownMenu,
+  DropdownMenuContent,
+  DropdownMenuGroup,
+  DropdownMenuItem,
+  DropdownMenuTrigger,
+} from '@documenso/ui/primitives/dropdown-menu';
+
+import { cn } from '../../lib/utils';
+import DocumentExpiryDialog from './document-expiry-dialog';
+
+type SignerActionDropdownProps = {
+  onDelete: () => void;
+  deleteDisabled?: boolean;
+  className?: string;
+};
+
+export function SignerActionDropdown({ deleteDisabled, className }: SignerActionDropdownProps) {
+  const [isExpiryDialogOpen, setExpiryDialogOpen] = useState(false);
+
+  return (
+    <>
+      <div className={cn('flex items-center justify-center', className)}>
+        <DropdownMenu>
+          <DropdownMenuTrigger>
+            <MoreHorizontal className="text-muted-foreground h-5 w-5" />
+          </DropdownMenuTrigger>
+          <DropdownMenuContent>
+            <DropdownMenuGroup>
+              <DropdownMenuItem className="gap-x-2" onClick={() => setExpiryDialogOpen(true)}>
+                <Timer className="h-4 w-4" />
+                Expiry
+              </DropdownMenuItem>
+              <DropdownMenuItem disabled={deleteDisabled} className="gap-x-2">
+                <Trash className="h-4 w-4" />
+                Delete
+              </DropdownMenuItem>
+            </DropdownMenuGroup>
+          </DropdownMenuContent>
+        </DropdownMenu>
+      </div>
+      <DocumentExpiryDialog open={isExpiryDialogOpen} onOpenChange={setExpiryDialogOpen} />
+    </>
+  );
+}
diff --git a/packages/ui/primitives/popover.tsx b/packages/ui/primitives/popover.tsx
index 62462322b..834aed5e7 100644
--- a/packages/ui/primitives/popover.tsx
+++ b/packages/ui/primitives/popover.tsx
@@ -92,4 +92,4 @@ const PopoverHover = ({ trigger, children, contentProps }: PopoverHoverProps) =>
   );
 };
 
-export { Popover, PopoverTrigger, PopoverContent, PopoverHover };
+export { Popover, PopoverContent, PopoverHover, PopoverTrigger };