diff --git a/apps/web/public/locales/en/app.json b/apps/web/public/locales/en/app.json
index 41a94c259..5f1a99b73 100644
--- a/apps/web/public/locales/en/app.json
+++ b/apps/web/public/locales/en/app.json
@@ -241,13 +241,6 @@
   "dangerZoneAccount": "Delete your account permanently. This action cannot be undone.",
   "upgradePromptTitle": "Upgrade to Pro",
   "upgradeOverlaySubtitle3": "Unlock these feature by upgrading to a Pro plan.",
-  "finalizeFeatureDescription": "Select a final date for your event and notify participants.",
-  "duplicateTitle": "Duplicate",
-  "duplicateFeatureDescription": "Reuse dates and settings of a poll to create a new one.",
-  "advancedSettingsTitle": "Advanced Settings",
-  "advancedSettingsDescription": "Hide participants, hide scores, require participant email address.",
-  "keepPollsIndefinitely": "Keep Polls Indefinitely",
-  "keepPollsIndefinitelyDescription": "Inactive polls will not be auto-deleted.",
   "verificationCodeSentTo": "We sent a verification code to <b>{email}</b>",
   "home": "Home",
   "groupPoll": "Group Poll",
@@ -282,5 +275,14 @@
   "fileTooLarge": "File too large",
   "fileTooLargeDescription": "Please upload a file smaller than 2MB.",
   "errorUploadPicture": "Failed to upload",
-  "errorUploadPictureDescription": "There was an issue uploading your picture. Please try again later."
+  "errorUploadPictureDescription": "There was an issue uploading your picture. Please try again later.",
+  "featureNameFinalize": "Finalize Poll",
+  "featureNameDuplicate": "Duplicate Poll",
+  "featureNameAdvancedSettings": "Advanced Settings",
+  "featureNameExtendedPollLifetime": "Extended Poll Lifetime",
+  "12months": "12 months",
+  "savePercentage": "Save {percentage}%",
+  "1month": "1 month",
+  "subscribe": "Subscribe",
+  "cancelAnytime": "Cancel anytime from your <a>billing page</a>."
 }
diff --git a/apps/web/src/app/[locale]/poll/[urlId]/pay-wall-dialog-content.tsx b/apps/web/src/app/[locale]/poll/[urlId]/pay-wall-dialog-content.tsx
index cb9f54f63..8c7774466 100644
--- a/apps/web/src/app/[locale]/poll/[urlId]/pay-wall-dialog-content.tsx
+++ b/apps/web/src/app/[locale]/poll/[urlId]/pay-wall-dialog-content.tsx
@@ -1,33 +1,38 @@
+import { pricingData } from "@rallly/billing/pricing";
 import { Badge } from "@rallly/ui/badge";
-import { Button } from "@rallly/ui/button";
-import { DialogClose, DialogContent } from "@rallly/ui/dialog";
+import { Dialog, DialogContent, DialogProps } from "@rallly/ui/dialog";
+import { RadioGroup, RadioGroupItem } from "@rallly/ui/radio-group";
 import { m } from "framer-motion";
-import {
-  CalendarCheck2Icon,
-  ClockIcon,
-  CopyIcon,
-  Settings2Icon,
-} from "lucide-react";
+import { CheckIcon } from "lucide-react";
 import Link from "next/link";
+import { useState } from "react";
 
 import { Trans } from "@/components/trans";
-import { usePlan } from "@/contexts/plan";
+import { UpgradeButton } from "@/components/upgrade-button";
 
-export function PayWallDialogContent({
-  children,
-}: {
-  children?: React.ReactNode;
-}) {
-  const plan = usePlan();
+const annualSavingsPercentage = (
+  ((pricingData.monthly.amount * 12 - pricingData.yearly.amount) /
+    (pricingData.monthly.amount * 12)) *
+  100
+).toFixed(0);
 
-  if (plan === "free") {
-    return (
+const yearlyPrice = (pricingData.yearly.amount / 100).toFixed(2);
+const monthlyPrice = (pricingData.monthly.amount / 100).toFixed(2);
+const monthlyPriceAnnualRate = (pricingData.yearly.amount / 100 / 12).toFixed(
+  2,
+);
+
+export function PayWallDialogContent(props: DialogProps) {
+  const [period, setPeriod] = useState("yearly");
+
+  return (
+    <Dialog {...props}>
       <DialogContent className="w-[600px] p-4">
-        <article>
-          <header className="p-4">
+        <div className="space-y-6">
+          <header className="pt-4">
             <m.div
               transition={{
-                delay: 0.5,
+                delay: 0.2,
                 duration: 0.4,
                 type: "spring",
                 bounce: 0.5,
@@ -41,111 +46,108 @@ export function PayWallDialogContent({
                 <Trans i18nKey="planPro" />
               </Badge>
             </m.div>
-            <h1 className="mb-1 mt-2 text-center text-xl font-bold">
+            <h1 className="mb-2 mt-4 text-center text-xl font-bold">
               <Trans defaults="Upgrade to Pro" i18nKey="upgradePromptTitle" />
             </h1>
-            <p className="text-muted-foreground text-center text-sm leading-relaxed">
+            <p className="text-muted-foreground mb-4 text-center text-sm leading-relaxed">
               <Trans
                 i18nKey="upgradeOverlaySubtitle3"
                 defaults="Unlock these feature by upgrading to a Pro plan."
               />
             </p>
-          </header>
-          <section className="rounded-lg border bg-gray-50">
-            <ul className="divide-y text-left">
-              <li className="flex items-start gap-x-4 p-4">
-                <div>
-                  <div className="inline-flex rounded-lg bg-indigo-100 p-2">
-                    <CalendarCheck2Icon className="size-4 text-indigo-600" />
-                  </div>
-                </div>
-                <div>
-                  <h3 className="mb-1 text-sm font-semibold">
-                    <Trans defaults="Finalize" i18nKey="finalize" />
-                  </h3>
-                  <p className="text-muted-foreground text-pretty text-sm leading-relaxed">
-                    <Trans
-                      i18nKey="finalizeFeatureDescription"
-                      defaults="Select a final date for your event and notify participants."
-                    />
-                  </p>
-                </div>
+            <ul className="grid grid-cols-2 justify-center gap-2 text-center text-sm font-medium">
+              <li>
+                <CheckIcon className="mr-2 inline-block size-4 text-green-600" />
+                <Trans i18nKey="featureNameFinalize" defaults="Finalize Poll" />
               </li>
-              <li className="flex items-start gap-x-4 p-4">
-                <div className="inline-flex rounded-lg bg-violet-100 p-2">
-                  <CopyIcon className="size-4 text-violet-600" />
-                </div>
-                <div>
-                  <h3 className="mb-1 text-sm font-semibold">
-                    <Trans defaults="Duplicate" i18nKey="duplicateTitle" />
-                  </h3>
-                  <p className="text-muted-foreground leading-rel text-pretty text-sm">
-                    <Trans
-                      i18nKey="duplicateFeatureDescription"
-                      defaults="Reuse dates and settings of a poll to create a new one."
-                    />
-                  </p>
-                </div>
+              <li>
+                <CheckIcon className="mr-2 inline-block size-4 text-green-600" />
+                <Trans
+                  i18nKey="featureNameDuplicate"
+                  defaults="Duplicate Poll"
+                />
               </li>
-              <li className="flex items-start gap-x-4 p-4">
-                <div>
-                  <div className="inline-flex rounded-lg bg-purple-100 p-2">
-                    <Settings2Icon className="size-4 text-purple-600" />
-                  </div>
-                </div>
-                <div>
-                  <h3 className="mb-1 text-sm font-semibold">
-                    <Trans
-                      defaults="Advanced Settings"
-                      i18nKey="advancedSettingsTitle"
-                    />
-                  </h3>
-                  <p className="text-muted-foreground leading-rel text-pretty text-sm">
-                    <Trans
-                      i18nKey="advancedSettingsDescription"
-                      defaults="Hide participants, hide scores, require participant email address."
-                    />
-                  </p>
-                </div>
+              <li>
+                <CheckIcon className="mr-2 inline-block size-4 text-green-600" />
+                <Trans
+                  i18nKey="featureNameAdvancedSettings"
+                  defaults="Advanced Settings"
+                />
               </li>
-              <li className="flex items-start gap-x-4 p-4">
-                <div>
-                  <div className="inline-flex rounded-lg bg-pink-100 p-2">
-                    <ClockIcon className="size-4 text-pink-600" />
-                  </div>
-                </div>
-                <div>
-                  <h3 className="mb-1 text-sm font-semibold">
-                    <Trans
-                      defaults="Keep Polls Indefinitely"
-                      i18nKey="keepPollsIndefinitely"
-                    />
-                  </h3>
-                  <p className="text-muted-foreground leading-rel text-pretty text-sm">
-                    <Trans
-                      i18nKey="keepPollsIndefinitelyDescription"
-                      defaults="Inactive polls will not be auto-deleted."
-                    />
-                  </p>
-                </div>
+              <li>
+                <CheckIcon className="mr-2 inline-block size-4 text-green-600" />
+                <Trans
+                  i18nKey="featureNameExtendedPollLifetime"
+                  defaults="Extended Poll Lifetime"
+                />
               </li>
             </ul>
+          </header>
+          <section>
+            <RadioGroup value={period} onValueChange={setPeriod}>
+              <li className="focus-within:ring-primary relative flex items-center justify-between rounded-lg border bg-gray-50 p-4 focus-within:ring-2">
+                <div className="space-y-1">
+                  <div className="flex items-center gap-4">
+                    <RadioGroupItem id="yearly" value="yearly" />
+                    <label className="text-base font-semibold" htmlFor="yearly">
+                      <span role="presentation" className="absolute inset-0" />
+                      <Trans defaults="12 months" i18nKey="12months" />
+                    </label>
+                    <Badge variant="green">
+                      <Trans
+                        defaults="Save {percentage}%"
+                        i18nKey="savePercentage"
+                        values={{ percentage: annualSavingsPercentage }}
+                      />
+                    </Badge>
+                  </div>
+                  <p className="text-muted-foreground flex items-baseline gap-1.5 pl-8 text-sm">
+                    <span>${yearlyPrice}</span>
+                    <span className="line-through opacity-50">
+                      ${((pricingData.monthly.amount * 12) / 100).toFixed(2)}
+                    </span>
+                  </p>
+                </div>
+                <p className="flex items-baseline gap-1">
+                  <span className="text-xl font-semibold">
+                    ${monthlyPriceAnnualRate}
+                  </span>
+                  <span className="text-muted-foreground text-sm">/ mo</span>
+                </p>
+              </li>
+              <li className="focus-within:ring-primary relative flex items-center justify-between rounded-lg border bg-gray-50 p-4 focus-within:ring-2">
+                <div className="flex items-center gap-4">
+                  <RadioGroupItem id="monthly" value="monthly" />
+                  <label className="text-base font-semibold" htmlFor="monthly">
+                    <span role="presentation" className="absolute inset-0" />
+                    <Trans defaults="1 month" i18nKey="1month" />
+                  </label>
+                </div>
+                <p className="flex items-baseline gap-1">
+                  <span className="text-xl font-semibold">${monthlyPrice}</span>
+                  <span className="text-muted-foreground text-sm">/ mo</span>
+                </p>
+              </li>
+            </RadioGroup>
           </section>
-          <footer className="mt-4 grid gap-2.5">
-            <Button variant="primary" asChild>
-              <Link href="/settings/billing">
-                <Trans i18nKey="upgrade" defaults="Upgrade" />
-              </Link>
-            </Button>
-            <DialogClose asChild>
-              <Button variant="ghost">
-                <Trans i18nKey="notToday" defaults="Not Today" />
-              </Button>
-            </DialogClose>
+          <footer className="space-y-4">
+            <div className="grid gap-2">
+              <UpgradeButton large annual={period === "yearly"}>
+                <Trans i18nKey="subscribe" defaults="Subscribe" />
+              </UpgradeButton>
+            </div>
+            <p className="text-muted-foreground text-center text-sm">
+              <Trans
+                i18nKey="cancelAnytime"
+                defaults="Cancel anytime from your <a>billing page</a>."
+                components={{
+                  a: <Link className="text-link" href="/settings/billing" />,
+                }}
+              />
+            </p>
           </footer>
-        </article>
+        </div>
       </DialogContent>
-    );
-  }
-  return <>{children}</>;
+    </Dialog>
+  );
 }
diff --git a/apps/web/src/components/poll/manage-poll.tsx b/apps/web/src/components/poll/manage-poll.tsx
index 0f168505b..774cb9920 100644
--- a/apps/web/src/components/poll/manage-poll.tsx
+++ b/apps/web/src/components/poll/manage-poll.tsx
@@ -27,11 +27,14 @@ import Link from "next/link";
 import * as React from "react";
 
 import { DuplicateDialog } from "@/app/[locale]/poll/[urlId]/duplicate-dialog";
+import { PayWallDialogContent } from "@/app/[locale]/poll/[urlId]/pay-wall-dialog-content";
 import { trpc } from "@/app/providers";
 import { FinalizePollDialog } from "@/components/poll/manage-poll/finalize-poll-dialog";
 import { ProFeatureBadge } from "@/components/pro-feature-badge";
 import { Trans } from "@/components/trans";
+import { usePlan } from "@/contexts/plan";
 import { usePoll } from "@/contexts/poll";
+import { usePostHog } from "@/utils/posthog";
 
 import { DeletePollDialog } from "./manage-poll/delete-poll-dialog";
 import { useCsvExporter } from "./manage-poll/use-csv-exporter";
@@ -144,6 +147,9 @@ const ManagePoll: React.FunctionComponent<{
   const [showDeletePollDialog, setShowDeletePollDialog] = React.useState(false);
   const duplicateDialog = useDialog();
   const finalizeDialog = useDialog();
+  const paywallDialog = useDialog();
+  const plan = usePlan();
+  const posthog = usePostHog();
   const { exportToCsv } = useCsvExporter();
 
   return (
@@ -161,37 +167,6 @@ const ManagePoll: React.FunctionComponent<{
           </Button>
         </DropdownMenuTrigger>
         <DropdownMenuContent align="end">
-          <>
-            {poll.status === "finalized" ? (
-              <DropdownMenuItem
-                onClick={() => {
-                  reopen.mutate({ pollId: poll.id });
-                }}
-              >
-                <Icon>
-                  <RotateCcwIcon />
-                </Icon>
-                <Trans i18nKey="reopenPoll" defaults="Reopen" />
-              </DropdownMenuItem>
-            ) : (
-              <>
-                <DropdownMenuItem
-                  disabled={!!poll.event}
-                  onClick={() => {
-                    finalizeDialog.trigger();
-                  }}
-                >
-                  <Icon>
-                    <CalendarCheck2Icon />
-                  </Icon>
-                  <Trans i18nKey="finishPoll" defaults="Finalize" />
-                  <ProFeatureBadge />
-                </DropdownMenuItem>
-                <PauseResumeToggle />
-              </>
-            )}
-          </>
-          <DropdownMenuSeparator />
           <DropdownMenuItem asChild>
             <Link href={`/poll/${poll.id}/edit-details`}>
               <DropdownMenuItemIconLabel icon={PencilIcon}>
@@ -214,6 +189,44 @@ const ManagePoll: React.FunctionComponent<{
             </Link>
           </DropdownMenuItem>
           <DropdownMenuSeparator />
+          <>
+            {poll.status === "finalized" ? (
+              <DropdownMenuItem
+                onClick={() => {
+                  reopen.mutate({ pollId: poll.id });
+                }}
+              >
+                <Icon>
+                  <RotateCcwIcon />
+                </Icon>
+                <Trans i18nKey="reopenPoll" defaults="Reopen" />
+              </DropdownMenuItem>
+            ) : (
+              <>
+                <DropdownMenuItem
+                  disabled={!!poll.event}
+                  onClick={() => {
+                    if (plan === "free") {
+                      paywallDialog.trigger();
+                      posthog?.capture("trigger paywall", {
+                        poll_id: poll.id,
+                        action: "finalize",
+                      });
+                    } else {
+                      finalizeDialog.trigger();
+                    }
+                  }}
+                >
+                  <Icon>
+                    <CalendarCheck2Icon />
+                  </Icon>
+                  <Trans i18nKey="finishPoll" defaults="Finalize" />
+                  <ProFeatureBadge />
+                </DropdownMenuItem>
+                <PauseResumeToggle />
+              </>
+            )}
+          </>
           <DropdownMenuSeparator />
           <DropdownMenuItem onClick={exportToCsv}>
             <DropdownMenuItemIconLabel icon={DownloadIcon}>
@@ -222,7 +235,15 @@ const ManagePoll: React.FunctionComponent<{
           </DropdownMenuItem>
           <DropdownMenuItem
             onClick={() => {
-              duplicateDialog.trigger();
+              if (plan === "free") {
+                paywallDialog.trigger();
+                posthog?.capture("trigger paywall", {
+                  poll_id: poll.id,
+                  action: "duplicate",
+                });
+              } else {
+                duplicateDialog.trigger();
+              }
             }}
           >
             <DropdownMenuItemIconLabel icon={CopyIcon}>
@@ -253,6 +274,7 @@ const ManagePoll: React.FunctionComponent<{
         {...duplicateDialog.dialogProps}
       />
       <FinalizePollDialog {...finalizeDialog.dialogProps} />
+      <PayWallDialogContent {...paywallDialog.dialogProps} />
     </>
   );
 };
diff --git a/apps/web/src/components/poll/manage-poll/finalize-poll-dialog.tsx b/apps/web/src/components/poll/manage-poll/finalize-poll-dialog.tsx
index a0c9700ec..0fe198ddb 100644
--- a/apps/web/src/components/poll/manage-poll/finalize-poll-dialog.tsx
+++ b/apps/web/src/components/poll/manage-poll/finalize-poll-dialog.tsx
@@ -24,7 +24,6 @@ import React from "react";
 import { useForm } from "react-hook-form";
 import { z } from "zod";
 
-import { PayWallDialogContent } from "@/app/[locale]/poll/[urlId]/pay-wall-dialog-content";
 import { trpc } from "@/app/providers";
 import { DateIconInner } from "@/components/date-icon";
 import { useParticipants } from "@/components/participants-provider";
@@ -206,61 +205,6 @@ export const FinalizePollForm = ({
             );
           }}
         />
-        {/* <FormField
-          control={form.control}
-          name="notify"
-          render={({ field }) => (
-            <FormItem>
-              <FormLabel htmlFor="notify" className="mb-4">
-                <Trans i18nKey="notify" defaults="Send a calendar invite to" />
-              </FormLabel>
-              <FormControl>
-                <RadioGroup onValueChange={field.onChange} value={field.value}>
-                  <Label className="flex items-center gap-4 font-normal">
-                    <RadioGroupItem value="all" />
-                    <Trans
-                      i18nKey="notifyAllParticipants"
-                      defaults="Everyone"
-                    />
-                  </Label>
-                  <Label className="flex items-center gap-4 font-normal">
-                    <RadioGroupItem value="attendees" />
-                    <Trans
-                      i18nKey="notifyAvailableParticipants"
-                      defaults="Attendees"
-                    />
-                  </Label>
-                  <Label className="flex items-center gap-4 font-normal">
-                    <RadioGroupItem value="none" />
-                    <Trans i18nKey="notifyNo" defaults="None" />
-                  </Label>
-                </RadioGroup>
-              </FormControl>
-              <FormDescription>
-                <Trans
-                  i18nKey="notifyDescription"
-                  defaults="Choose which participants should receive a calendar invite"
-                />
-              </FormDescription>
-              {participantsWithoutEmails.length ? (
-                <Alert>
-                  <AlertCircleIcon className="size-4" />
-                  <AlertDescription>
-                    <Trans
-                      i18nKey="missingEmailsAlert"
-                      defaults="The following participants have not provided an email address."
-                    />
-                  </AlertDescription>
-                  <AlertDescription>
-                    {participantsWithoutEmails.map((participant) => (
-                      <div key={participant.id}>{participant.name}</div>
-                    ))}
-                  </AlertDescription>
-                </Alert>
-              ) : null}
-            </FormItem>
-          )}
-        /> */}
       </form>
     </Form>
   );
@@ -276,47 +220,45 @@ export function FinalizePollDialog(props: DialogProps) {
   });
   return (
     <Dialog {...props}>
-      <PayWallDialogContent>
-        <DialogContent size="2xl">
-          <DialogHeader>
-            <DialogTitle>
-              <Trans i18nKey="finalize" />
-            </DialogTitle>
-            <DialogDescription>
-              <Trans
-                i18nKey="finalizeDescription"
-                defaults="Select a final date for your event."
-              />
-            </DialogDescription>
-          </DialogHeader>
-          <FinalizePollForm
-            name="finalize-form"
-            onSubmit={(data) => {
-              scheduleEvent.mutate({
-                pollId: poll.id,
-                optionId: data.selectedOptionId,
-                notify: data.notify,
-              });
-              props.onOpenChange?.(false);
-            }}
-          />
-          <DialogFooter>
-            <DialogClose asChild>
-              <Button>
-                <Trans i18nKey="cancel" />
-              </Button>
-            </DialogClose>
-            <Button
-              loading={scheduleEvent.isLoading}
-              type="submit"
-              form="finalize-form"
-              variant="primary"
-            >
-              <Trans i18nKey="finalize" />
+      <DialogContent size="2xl">
+        <DialogHeader>
+          <DialogTitle>
+            <Trans i18nKey="finalize" />
+          </DialogTitle>
+          <DialogDescription>
+            <Trans
+              i18nKey="finalizeDescription"
+              defaults="Select a final date for your event."
+            />
+          </DialogDescription>
+        </DialogHeader>
+        <FinalizePollForm
+          name="finalize-form"
+          onSubmit={(data) => {
+            scheduleEvent.mutate({
+              pollId: poll.id,
+              optionId: data.selectedOptionId,
+              notify: data.notify,
+            });
+            props.onOpenChange?.(false);
+          }}
+        />
+        <DialogFooter>
+          <DialogClose asChild>
+            <Button>
+              <Trans i18nKey="cancel" />
             </Button>
-          </DialogFooter>
-        </DialogContent>
-      </PayWallDialogContent>
+          </DialogClose>
+          <Button
+            loading={scheduleEvent.isLoading}
+            type="submit"
+            form="finalize-form"
+            variant="primary"
+          >
+            <Trans i18nKey="finalize" />
+          </Button>
+        </DialogFooter>
+      </DialogContent>
     </Dialog>
   );
 }
diff --git a/apps/web/src/components/upgrade-button.tsx b/apps/web/src/components/upgrade-button.tsx
index f4073631d..c2217fddc 100644
--- a/apps/web/src/components/upgrade-button.tsx
+++ b/apps/web/src/components/upgrade-button.tsx
@@ -8,7 +8,8 @@ import { usePostHog } from "@/utils/posthog";
 export const UpgradeButton = ({
   children,
   annual,
-}: React.PropsWithChildren<{ annual?: boolean }>) => {
+  large,
+}: React.PropsWithChildren<{ annual?: boolean; large?: boolean }>) => {
   const posthog = usePostHog();
 
   return (
@@ -24,6 +25,7 @@ export const UpgradeButton = ({
         value={window.location.pathname}
       />
       <Button
+        size={large ? "lg" : "default"}
         className="w-full"
         type="submit"
         variant="primary"