diff --git a/package-lock.json b/package-lock.json
index eb83625..e871aa4 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -34,8 +34,9 @@
         "micro": "^10.0.1",
         "micro-cors": "^0.1.1",
         "next": "^13.3.0",
-        "next-auth": "^4.21.0",
+        "next-auth": "^4.22.1",
         "posthog-js": "^1.53.4",
+        "posthog-node": "^3.1.0",
         "react": "18.2.0",
         "react-dom": "18.2.0",
         "react-media-recorder": "^1.6.6",
@@ -5349,9 +5350,9 @@
       }
     },
     "node_modules/next-auth": {
-      "version": "4.22.0",
-      "resolved": "https://registry.npmjs.org/next-auth/-/next-auth-4.22.0.tgz",
-      "integrity": "sha512-08+kjnDoE7aQ52O996x6cwA3ffc2CbHIkrCgLYhbE+aDIJBKI0oA9UbIEIe19/+ODYJgpAHHOtJx4izmsgaVag==",
+      "version": "4.22.1",
+      "resolved": "https://registry.npmjs.org/next-auth/-/next-auth-4.22.1.tgz",
+      "integrity": "sha512-NTR3f6W7/AWXKw8GSsgSyQcDW6jkslZLH8AiZa5PQ09w1kR8uHtR9rez/E9gAq/o17+p0JYHE8QjF3RoniiObA==",
       "dependencies": {
         "@babel/runtime": "^7.20.13",
         "@panva/hkdf": "^1.0.2",
@@ -5858,6 +5859,26 @@
         "rrweb-snapshot": "^1.1.14"
       }
     },
+    "node_modules/posthog-node": {
+      "version": "3.1.0",
+      "resolved": "https://registry.npmjs.org/posthog-node/-/posthog-node-3.1.0.tgz",
+      "integrity": "sha512-hXhkDWigzNYgkfLpd3HbfCD0h1/zP19pPXEba2Daf6xCerrFxc7ixMDtXwCQMXOmJNvrcoVMvrjULpfKHN11vA==",
+      "dependencies": {
+        "axios": "^0.27.0"
+      },
+      "engines": {
+        "node": ">=15.0.0"
+      }
+    },
+    "node_modules/posthog-node/node_modules/axios": {
+      "version": "0.27.2",
+      "resolved": "https://registry.npmjs.org/axios/-/axios-0.27.2.tgz",
+      "integrity": "sha512-t+yRIyySRTp/wua5xEr+z1q60QmLq8ABsS5O9Me1AsE5dfKqgnCFzwiCZZ/cGNd1lq4/7akDWMxdhVlucjmnOQ==",
+      "dependencies": {
+        "follow-redirects": "^1.14.9",
+        "form-data": "^4.0.0"
+      }
+    },
     "node_modules/preact": {
       "version": "10.13.2",
       "resolved": "https://registry.npmjs.org/preact/-/preact-10.13.2.tgz",
@@ -11126,9 +11147,9 @@
       }
     },
     "next-auth": {
-      "version": "4.22.0",
-      "resolved": "https://registry.npmjs.org/next-auth/-/next-auth-4.22.0.tgz",
-      "integrity": "sha512-08+kjnDoE7aQ52O996x6cwA3ffc2CbHIkrCgLYhbE+aDIJBKI0oA9UbIEIe19/+ODYJgpAHHOtJx4izmsgaVag==",
+      "version": "4.22.1",
+      "resolved": "https://registry.npmjs.org/next-auth/-/next-auth-4.22.1.tgz",
+      "integrity": "sha512-NTR3f6W7/AWXKw8GSsgSyQcDW6jkslZLH8AiZa5PQ09w1kR8uHtR9rez/E9gAq/o17+p0JYHE8QjF3RoniiObA==",
       "requires": {
         "@babel/runtime": "^7.20.13",
         "@panva/hkdf": "^1.0.2",
@@ -11451,6 +11472,25 @@
         "rrweb-snapshot": "^1.1.14"
       }
     },
+    "posthog-node": {
+      "version": "3.1.0",
+      "resolved": "https://registry.npmjs.org/posthog-node/-/posthog-node-3.1.0.tgz",
+      "integrity": "sha512-hXhkDWigzNYgkfLpd3HbfCD0h1/zP19pPXEba2Daf6xCerrFxc7ixMDtXwCQMXOmJNvrcoVMvrjULpfKHN11vA==",
+      "requires": {
+        "axios": "^0.27.0"
+      },
+      "dependencies": {
+        "axios": {
+          "version": "0.27.2",
+          "resolved": "https://registry.npmjs.org/axios/-/axios-0.27.2.tgz",
+          "integrity": "sha512-t+yRIyySRTp/wua5xEr+z1q60QmLq8ABsS5O9Me1AsE5dfKqgnCFzwiCZZ/cGNd1lq4/7akDWMxdhVlucjmnOQ==",
+          "requires": {
+            "follow-redirects": "^1.14.9",
+            "form-data": "^4.0.0"
+          }
+        }
+      }
+    },
     "preact": {
       "version": "10.13.2",
       "resolved": "https://registry.npmjs.org/preact/-/preact-10.13.2.tgz",
diff --git a/package.json b/package.json
index 9067ab7..ddcd95e 100644
--- a/package.json
+++ b/package.json
@@ -42,8 +42,9 @@
     "micro": "^10.0.1",
     "micro-cors": "^0.1.1",
     "next": "^13.3.0",
-    "next-auth": "^4.21.0",
+    "next-auth": "^4.22.1",
     "posthog-js": "^1.53.4",
+    "posthog-node": "^3.1.0",
     "react": "18.2.0",
     "react-dom": "18.2.0",
     "react-media-recorder": "^1.6.6",
diff --git a/src/components/NewVideoMenu.tsx b/src/components/NewVideoMenu.tsx
index e311f15..f574a3f 100644
--- a/src/components/NewVideoMenu.tsx
+++ b/src/components/NewVideoMenu.tsx
@@ -5,22 +5,36 @@ import { useAtom } from "jotai";
 import recordVideoModalOpen from "~/atoms/recordVideoModalOpen";
 import paywallAtom from "~/atoms/paywallAtom";
 import { useSession } from "next-auth/react";
+import { usePostHog } from "posthog-js/react";
 
 export default function NewVideoMenu() {
   const [, setRecordOpen] = useAtom(recordVideoModalOpen);
   const [, setUploadOpen] = useAtom(uploadVideoModalOpen);
   const [, setPaywallOpen] = useAtom(paywallAtom);
   const { data: session } = useSession();
+  const posthog = usePostHog();
 
   const openRecordModal = () => {
     setRecordOpen(true);
+
+    posthog?.capture("open record video modal", {
+      stripeSubscriptionStatus: session?.user.stripeSubscriptionStatus,
+    });
   };
 
   const openUploadModal = () => {
     if (session?.user.stripeSubscriptionStatus === "active") {
       setUploadOpen(true);
+
+      posthog?.capture("open upload video modal", {
+        stripeSubscriptionStatus: session?.user.stripeSubscriptionStatus,
+      });
     } else {
       setPaywallOpen(true);
+
+      posthog?.capture("hit video upload paywall", {
+        stripeSubscriptionStatus: session?.user.stripeSubscriptionStatus,
+      });
     }
   };
 
diff --git a/src/components/Paywall.tsx b/src/components/Paywall.tsx
index 6c73dc0..3b13e40 100644
--- a/src/components/Paywall.tsx
+++ b/src/components/Paywall.tsx
@@ -7,6 +7,7 @@ import { api } from "~/utils/api";
 import { useRouter } from "next/router";
 import { CheckIcon } from "@heroicons/react/20/solid";
 import Tooltip from "~/components/Tooltip";
+import { usePostHog } from "posthog-js/react";
 
 export default function Paywall() {
   const { mutateAsync: createCheckoutSession } =
@@ -14,9 +15,12 @@ export default function Paywall() {
   const router = useRouter();
   const [open, setOpen] = useAtom(paywallAtom);
   const [billedAnnually, setBilledAnnually] = useState<boolean>(false);
+  const posthog = usePostHog();
 
   function closeModal() {
     setOpen(false);
+
+    posthog?.capture("close paywall");
   }
 
   const handleCheckout = async () => {
@@ -26,6 +30,12 @@ export default function Paywall() {
     }
   };
 
+  const toggleBillingCycle = () => {
+    setBilledAnnually(!billedAnnually);
+
+    posthog?.capture("change billing cycle");
+  };
+
   return (
     <Transition appear show={open} as={Fragment}>
       <Dialog as="div" className="relative z-10" onClose={closeModal}>
@@ -85,7 +95,7 @@ export default function Paywall() {
                           <span className=" svelte-10wstod">Monthly</span>
                           <label className="group relative flex cursor-pointer items-center gap-2 text-sm font-medium text-gray-600">
                             <input
-                              onChange={() => setBilledAnnually(!billedAnnually)}
+                              onChange={toggleBillingCycle}
                               checked={billedAnnually}
                               type="checkbox"
                               className="peer absolute left-1/2 hidden h-full w-full -translate-x-1/2 rounded-md"
diff --git a/src/components/ProfileMenu.tsx b/src/components/ProfileMenu.tsx
index a99021e..80248cd 100644
--- a/src/components/ProfileMenu.tsx
+++ b/src/components/ProfileMenu.tsx
@@ -3,12 +3,26 @@ import { Fragment } from "react";
 import { signOut, useSession } from "next-auth/react";
 import { useRouter } from "next/router";
 import { api } from "~/utils/api";
+import { usePostHog } from "posthog-js/react";
 
 export default function ProfileMenu() {
   const { mutateAsync: createBillingPortalSession } =
     api.stripe.createBillingPortalSession.useMutation();
   const { push } = useRouter();
   const { data: session } = useSession();
+  const posthog = usePostHog();
+
+  const openBillingSettings = () => {
+    void createBillingPortalSession().then(({ billingPortalUrl }) => {
+      if (billingPortalUrl) {
+        void push(billingPortalUrl);
+      }
+    });
+
+    posthog?.capture("billing settings opened", {
+      stripeSubscriptionStatus: session?.user.stripeSubscriptionStatus,
+    });
+  };
 
   return (
     <Menu as="div" className="relative inline-block text-left">
@@ -34,15 +48,7 @@ export default function ProfileMenu() {
             <Menu.Item>
               {({ active }) => (
                 <div
-                  onClick={() => {
-                    void createBillingPortalSession().then(
-                      ({ billingPortalUrl }) => {
-                        if (billingPortalUrl) {
-                          void push(billingPortalUrl);
-                        }
-                      }
-                    );
-                  }}
+                  onClick={openBillingSettings}
                   className={`mx-2 flex h-8 w-40 cursor-pointer flex-row content-center rounded-md p-2 ${
                     active ? "bg-gray-100" : ""
                   }`}
diff --git a/src/components/Recorder.tsx b/src/components/Recorder.tsx
index 40bec3b..15e1718 100644
--- a/src/components/Recorder.tsx
+++ b/src/components/Recorder.tsx
@@ -15,6 +15,7 @@ import { TRPCClientError } from "@trpc/client";
 import { useAtom } from "jotai/index";
 import paywallAtom from "~/atoms/paywallAtom";
 import recordVideoModalOpen from "~/atoms/recordVideoModalOpen";
+import { usePostHog } from "posthog-js/react";
 
 interface Props {
   closeModal: () => void;
@@ -45,6 +46,7 @@ export default function Recorder({ closeModal, step, setStep }: Props) {
   const [duration, setDuration] = useState<number>(0);
   const [, setPaywallOpen] = useAtom(paywallAtom);
   const videoRef = useRef<null | HTMLVideoElement>(null);
+  const posthog = usePostHog();
 
   const handleRecording = async () => {
     const screenStream = await navigator.mediaDevices.getDisplayMedia({
@@ -80,6 +82,8 @@ export default function Recorder({ closeModal, step, setStep }: Props) {
     recorderRef.current.startRecording();
 
     setStep("in");
+
+    posthog?.capture("recorder: start video recording");
   };
 
   const handleStop = () => {
@@ -98,6 +102,8 @@ export default function Recorder({ closeModal, step, setStep }: Props) {
     });
 
     setStep("post");
+
+    posthog?.capture("recorder: video recording finished");
   };
 
   const handleDelete = () => {
@@ -109,6 +115,8 @@ export default function Recorder({ closeModal, step, setStep }: Props) {
 
     closeModal();
     setStep("pre");
+
+    posthog?.capture("recorder: video deleted");
   };
 
   const handlePause = () => {
@@ -119,6 +127,7 @@ export default function Recorder({ closeModal, step, setStep }: Props) {
       } else {
         recorderRef.current.pauseRecording();
       }
+      posthog?.capture("recorder: recording paused/resumed", { pause });
       setPause(!pause);
     }
   };
@@ -146,6 +155,8 @@ export default function Recorder({ closeModal, step, setStep }: Props) {
         "Recording - " + dayjs().format("D MMM YYYY") + ".webm";
       invokeSaveAsDialog(blob, dateString);
     }
+
+    posthog?.capture("recorder: video downloaded");
   };
 
   const generateThumbnail = async (video: HTMLVideoElement) => {
@@ -187,6 +198,7 @@ export default function Recorder({ closeModal, step, setStep }: Props) {
         .then(() => {
           void router.push("share/" + id);
           setRecordOpen(false);
+          posthog?.capture("recorder: video uploaded");
         })
         .catch((err) => {
           console.error(err);
@@ -197,6 +209,7 @@ export default function Recorder({ closeModal, step, setStep }: Props) {
           err.message ===
           "Sorry, you have reached the maximum video upload limit on our free tier. Please upgrade to upload more."
         ) {
+          posthog?.capture("recorder: video upload paywall hit");
           setPaywallOpen(true);
         }
       } else {
@@ -325,6 +338,8 @@ export default function Recorder({ closeModal, step, setStep }: Props) {
             <video
               src={URL.createObjectURL(blob)}
               controls
+              onPlay={() => posthog?.capture("recorder: played preview video")}
+              onPause={() => posthog?.capture("recorder: paused preview video")}
               ref={videoRef}
               className="mb-4 w-[75vw]"
             />
@@ -374,7 +389,10 @@ export default function Recorder({ closeModal, step, setStep }: Props) {
             <button
               type="button"
               className="ml-auto inline-flex items-center rounded-md bg-indigo-500 px-4 py-2 text-sm font-semibold leading-6 text-white shadow transition duration-150 ease-in-out hover:bg-indigo-400 disabled:cursor-not-allowed"
-              onClick={() => void closeModal()}
+              onClick={() => {
+                posthog?.capture("recorder: closed post-modal");
+                void closeModal();
+              }}
             >
               Close
             </button>
diff --git a/src/components/ShareModal.tsx b/src/components/ShareModal.tsx
index 5b89157..b63dfa3 100644
--- a/src/components/ShareModal.tsx
+++ b/src/components/ShareModal.tsx
@@ -3,6 +3,7 @@ import { Fragment, useState } from "react";
 import { ModernSwitch } from "~/components/ModernSwitch";
 import { api, type RouterOutputs } from "~/utils/api";
 import ExpireDateSelectMenu from "~/components/ExpireDateSelectMenu";
+import { usePostHog } from "posthog-js/react";
 
 interface Props {
   video: RouterOutputs["video"]["get"];
@@ -11,6 +12,23 @@ interface Props {
 export function ShareModal({ video }: Props) {
   const utils = api.useContext();
   const [open, setOpen] = useState<boolean>(false);
+  const posthog = usePostHog();
+
+  const openModal = () => {
+    setOpen(true);
+    posthog?.capture("open video share modal", {
+      videoSharing: video.sharing,
+      videoId: video.id,
+    });
+  };
+
+  const closeModal = () => {
+    setOpen(false);
+    posthog?.capture("close video share modal", {
+      videoSharing: video.sharing,
+      videoId: video.id,
+    });
+  };
 
   const setSharingMutation = api.video.setSharing.useMutation({
     onMutate: async ({ videoId, sharing }) => {
@@ -58,23 +76,24 @@ export function ShareModal({ video }: Props) {
     setTimeout(() => {
       setLinkCopied(false);
     }, 5000);
+
+    posthog?.capture("public video link copied", {
+      videoSharing: video.sharing,
+      videoId: video.id,
+    });
   };
 
   return (
     <>
       <span
-        onClick={() => setOpen(true)}
+        onClick={openModal}
         className="ml-4 cursor-pointer rounded border border-[#0000001a] px-2 py-2 text-sm text-[#292d34] hover:bg-[#fafbfc]"
       >
         Share
       </span>
 
       <Transition appear show={open} as={Fragment}>
-        <Dialog
-          as="div"
-          className="relative z-10"
-          onClose={() => setOpen(false)}
-        >
+        <Dialog as="div" className="relative z-10" onClose={closeModal}>
           <Transition.Child
             as={Fragment}
             enter="ease-out duration-300"
@@ -146,19 +165,6 @@ export function ShareModal({ video }: Props) {
                               }
                             />
                           </div>
-                          {/*<div className="mt-3 flex h-6 items-center justify-between">*/}
-                          {/*  <span>Share link with search engines</span>*/}
-                          {/*  <ModernSwitch*/}
-                          {/*    enabled={video.linkShareSeo}*/}
-                          {/*    toggle={() => console.log("test")}*/}
-                          {/*  />*/}
-                          {/*</div>*/}
-                          {/*<div className="mt-3 flex h-6 items-center justify-between">*/}
-                          {/*  <span>Embed code</span>*/}
-                          {/*  <button className="h-6 rounded border border-solid border-[#d5d9df] bg-white px-[7px] font-medium">*/}
-                          {/*    Copy code*/}
-                          {/*  </button>*/}
-                          {/*</div>*/}
                         </div>
                       </>
                     ) : null}
diff --git a/src/components/VideoMoreMenu.tsx b/src/components/VideoMoreMenu.tsx
index e43c802..da469e8 100644
--- a/src/components/VideoMoreMenu.tsx
+++ b/src/components/VideoMoreMenu.tsx
@@ -8,6 +8,7 @@ import {
   TrashIcon,
 } from "@radix-ui/react-icons";
 import { useRouter } from "next/router";
+import { usePostHog } from "posthog-js/react";
 
 interface Props {
   video: RouterOutputs["video"]["get"];
@@ -18,6 +19,7 @@ export default function VideoMoreMenu({ video }: Props) {
   const [renameMenuOpen, setRenameMenuOpen] = useState<boolean>(false);
   const utils = api.useContext();
   const router = useRouter();
+  const posthog = usePostHog();
 
   const items = [
     {
@@ -42,7 +44,10 @@ export default function VideoMoreMenu({ video }: Props) {
               a.download = video.title;
               a.click();
             });
-            //window.location.href = response.url;
+          });
+
+          posthog?.capture("download existing video", {
+            videoId: video.id,
           });
         },
       },
diff --git a/src/components/VideoRecordModal.tsx b/src/components/VideoRecordModal.tsx
index 35cf4c1..80181ae 100644
--- a/src/components/VideoRecordModal.tsx
+++ b/src/components/VideoRecordModal.tsx
@@ -4,10 +4,12 @@ const Recorder = dynamic(() => import("~/components/Recorder"), { ssr: false });
 import dynamic from "next/dynamic";
 import { useAtom } from "jotai";
 import recordVideoModalOpen from "~/atoms/recordVideoModalOpen";
+import { usePostHog } from "posthog-js/react";
 
 export default function VideoRecordModal() {
   const [open, setOpen] = useAtom(recordVideoModalOpen);
   const [step, setStep] = useState<"pre" | "in" | "post">("pre");
+  const posthog = usePostHog();
 
   function closeModal() {
     setOpen(false);
@@ -15,6 +17,8 @@ export default function VideoRecordModal() {
 
   const handleClose = () => {
     if (step === "pre") closeModal();
+
+    posthog?.capture("cancel video pre-recording");
   };
 
   return (
diff --git a/src/components/VideoUploadModal.tsx b/src/components/VideoUploadModal.tsx
index 440ec9b..fb5c826 100644
--- a/src/components/VideoUploadModal.tsx
+++ b/src/components/VideoUploadModal.tsx
@@ -5,6 +5,8 @@ import axios from "axios";
 import { useRouter } from "next/router";
 import { useAtom } from "jotai";
 import uploadVideoModalOpen from "~/atoms/uploadVideoModalOpen";
+import { usePostHog } from "posthog-js/react";
+import { useSession } from "next-auth/react";
 
 export default function VideoUploadModal() {
   const [open, setOpen] = useAtom(uploadVideoModalOpen);
@@ -14,6 +16,8 @@ export default function VideoUploadModal() {
   const getSignedUrl = api.video.getUploadUrl.useMutation();
   const apiUtils = api.useContext();
   const videoRef = useRef<null | HTMLVideoElement>(null);
+  const posthog = usePostHog();
+  const { data: session } = useSession();
 
   const handleFileChange = (e: ChangeEvent<HTMLInputElement>): void => {
     if (e.target.files) {
@@ -33,6 +37,10 @@ export default function VideoUploadModal() {
 
   function closeModal() {
     setOpen(false);
+
+    posthog?.capture("cancel video upload", {
+      stripeSubscriptionStatus: session?.user.stripeSubscriptionStatus,
+    });
   }
 
   const handleSubmit = async (): Promise<void> => {
diff --git a/src/pages/_app.tsx b/src/pages/_app.tsx
index b70ce29..c59dbf5 100644
--- a/src/pages/_app.tsx
+++ b/src/pages/_app.tsx
@@ -1,14 +1,15 @@
 import { type AppType } from "next/app";
 import { type Session } from "next-auth";
-import { SessionProvider } from "next-auth/react";
+import { SessionProvider, useSession } from "next-auth/react";
 
 import { api } from "~/utils/api";
 
 import "~/styles/globals.css";
 import CrispChat from "~/components/CrispChat";
 import posthog from "posthog-js";
-import { PostHogProvider } from "posthog-js/react";
+import { PostHogProvider, usePostHog } from "posthog-js/react";
 import { env } from "~/env.mjs";
+import { type ReactNode, useEffect } from "react";
 
 // Check that PostHog is client-side (used to handle Next.js SSR)
 if (typeof window !== "undefined") {
@@ -28,11 +29,38 @@ const MyApp: AppType<{ session: Session | null }> = ({
   return (
     <SessionProvider session={session}>
       <PostHogProvider client={posthog}>
-        <Component {...pageProps} />
+        <PostHogIdentificationWrapper>
+          <Component {...pageProps} />
+        </PostHogIdentificationWrapper>
         <CrispChat />
       </PostHogProvider>
     </SessionProvider>
   );
 };
 
+const PostHogIdentificationWrapper = ({
+  children,
+}: {
+  children: ReactNode;
+}) => {
+  const { data: session, status } = useSession();
+  const posthog = usePostHog();
+
+  useEffect(() => {
+    if (!posthog) return;
+    if (status === "authenticated") {
+      const { id, name, email, stripeSubscriptionStatus } = session?.user;
+      posthog.identify(id, {
+        name,
+        email,
+        stripeSubscriptionStatus,
+      });
+    } else if (status === "unauthenticated") {
+      posthog.reset();
+    }
+  }, [posthog, session, status]);
+
+  return <div>{children}</div>;
+};
+
 export default api.withTRPC(MyApp);
diff --git a/src/pages/api/webhooks/stripe.ts b/src/pages/api/webhooks/stripe.ts
index 828bb9a..a7d4c8c 100644
--- a/src/pages/api/webhooks/stripe.ts
+++ b/src/pages/api/webhooks/stripe.ts
@@ -9,6 +9,7 @@ import {
   handleSubscriptionCreatedOrUpdated,
 } from "~/server/stripe-webhook-handlers";
 import { stripe } from "~/server/stripe";
+import { posthog } from "~/server/posthog";
 
 // Stripe requires the raw body to construct the event.
 export const config = {
@@ -41,6 +42,7 @@ export default async function handler(
             event,
             stripe,
             prisma,
+            posthog,
           });
           break;
         case "customer.subscription.created":
@@ -48,6 +50,7 @@ export default async function handler(
           await handleSubscriptionCreatedOrUpdated({
             event,
             prisma,
+            posthog,
           });
           break;
         case "customer.subscription.updated":
@@ -55,6 +58,7 @@ export default async function handler(
           await handleSubscriptionCreatedOrUpdated({
             event,
             prisma,
+            posthog,
           });
           break;
         case "invoice.payment_failed":
@@ -63,6 +67,17 @@ export default async function handler(
           // Use this webhook to notify your user that their payment has
           // failed and to retrieve new card details.
           // Can also have Stripe send an email to the customer notifying them of the failure. See settings: https://dashboard.stripe.com/settings/billing/automatic
+
+          const subscription = event.data.object as Stripe.Subscription;
+          const userId = subscription.metadata.userId;
+
+          if (userId) {
+            posthog.capture({
+              distinctId: userId,
+              event: "stripe invoice.payment_failed",
+            });
+            void posthog.shutdownAsync();
+          }
           break;
         case "customer.subscription.deleted":
           // handle subscription cancelled automatically based
@@ -70,6 +85,7 @@ export default async function handler(
           await handleSubscriptionCanceled({
             event,
             prisma,
+            posthog,
           });
           break;
         default:
diff --git a/src/pages/share/[videoId].tsx b/src/pages/share/[videoId].tsx
index c591cdd..31535ad 100644
--- a/src/pages/share/[videoId].tsx
+++ b/src/pages/share/[videoId].tsx
@@ -11,17 +11,30 @@ import { ShareModal } from "~/components/ShareModal";
 import { useSession } from "next-auth/react";
 import VideoMoreMenu from "~/components/VideoMoreMenu";
 import ProfileMenu from "~/components/ProfileMenu";
+import { usePostHog } from "posthog-js/react";
 
 const VideoList: NextPage = () => {
   const router = useRouter();
   const { status, data: session } = useSession();
   const { videoId } = router.query as { videoId: string };
+  const posthog = usePostHog();
 
   const { data: video, isLoading } = api.video.get.useQuery(
     { videoId },
     {
       enabled: router.isReady,
       refetchOnWindowFocus: false,
+      retry: (failureCount, error) => {
+        if (error?.data?.code === "FORBIDDEN") return false;
+        else return failureCount < 2;
+      },
+      onError: (err) => {
+        if (err?.data?.code === "FORBIDDEN") {
+          posthog?.capture("video page: FORBIDDEN");
+        } else if (err?.data?.code === "NOT_FOUND") {
+          posthog?.capture("video page: NOT_FOUND");
+        }
+      },
     }
   );
 
@@ -33,7 +46,13 @@ const VideoList: NextPage = () => {
         </span>
         <span className="mt-3 max-w-[80%] text-center text-sm">
           To create your own public recordings,{" "}
-          <Link href="/sign-in" className="pointer text-[#4169e1] underline">
+          <Link
+            onClick={() =>
+              posthog?.capture("click sign-up from video error page")
+            }
+            href="/sign-in"
+            className="pointer text-[#4169e1] underline"
+          >
             create an account
           </Link>{" "}
           for free!
@@ -78,6 +97,30 @@ const VideoList: NextPage = () => {
                 width="100%"
                 height="100%"
                 controls={true}
+                onPlay={() =>
+                  posthog?.capture("play video", {
+                    videoId: video.id,
+                    videoCreatedAt: video.createdAt,
+                    videoUpdatedAt: video.updatedAt,
+                    videoUser: video.user.id,
+                    videoSharing: video.sharing,
+                    videoDeleteAfterLinkExpires:
+                      video.delete_after_link_expires,
+                    videoShareLinkExpiresAt: video.shareLinkExpiresAt,
+                  })
+                }
+                onPause={() =>
+                  posthog?.capture("pause video", {
+                    videoId: video.id,
+                    videoCreatedAt: video.createdAt,
+                    videoUpdatedAt: video.updatedAt,
+                    videoUser: video.user.id,
+                    videoSharing: video.sharing,
+                    videoDeleteAfterLinkExpires:
+                      video.delete_after_link_expires,
+                    videoShareLinkExpiresAt: video.shareLinkExpiresAt,
+                  })
+                }
                 url={video.video_url}
               />
             )}
diff --git a/src/pages/videos.tsx b/src/pages/videos.tsx
index 2365cdd..03e5766 100644
--- a/src/pages/videos.tsx
+++ b/src/pages/videos.tsx
@@ -16,6 +16,7 @@ import uploadVideoModalOpen from "~/atoms/uploadVideoModalOpen";
 import recordVideoModalOpen from "~/atoms/recordVideoModalOpen";
 import Paywall from "~/components/Paywall";
 import paywallAtom from "~/atoms/paywallAtom";
+import { usePostHog } from "posthog-js/react";
 
 const VideoList: NextPage = () => {
   const [, setRecordOpen] = useAtom(recordVideoModalOpen);
@@ -24,6 +25,7 @@ const VideoList: NextPage = () => {
   const router = useRouter();
   const { status, data: session } = useSession();
   const { data: videos, isLoading } = api.video.getAll.useQuery();
+  const posthog = usePostHog();
 
   if (status === "unauthenticated") {
     void router.replace("/sign-in");
@@ -31,13 +33,28 @@ const VideoList: NextPage = () => {
 
   const openRecordModal = () => {
     setRecordOpen(true);
+
+    posthog?.capture("open record video modal", {
+      stripeSubscriptionStatus: session?.user.stripeSubscriptionStatus,
+      cta: "empty video list page",
+    });
   };
 
   const openUploadModal = () => {
     if (session?.user.stripeSubscriptionStatus === "active") {
       setUploadOpen(true);
+
+      posthog?.capture("open upload video modal", {
+        stripeSubscriptionStatus: session?.user.stripeSubscriptionStatus,
+        cta: "empty video list page",
+      });
     } else {
       setPaywallOpen(true);
+
+      posthog?.capture("hit video upload paywall", {
+        stripeSubscriptionStatus: session?.user.stripeSubscriptionStatus,
+        cta: "empty video list page",
+      });
     }
   };
 
diff --git a/src/server/api/routers/stripe.ts b/src/server/api/routers/stripe.ts
index 84edf28..65a0df9 100644
--- a/src/server/api/routers/stripe.ts
+++ b/src/server/api/routers/stripe.ts
@@ -6,9 +6,64 @@ import { z } from "zod";
 export const stripeRouter = createTRPCRouter({
   createCheckoutSession: protectedProcedure
     .input(z.object({ billedAnnually: z.boolean() }))
-    .mutation(async ({ ctx, input }) => {
-      const { stripe, session, prisma, req } = ctx;
+    .mutation(
+      async ({ ctx: { prisma, stripe, session, req, posthog }, input }) => {
+        const customerId = await getOrCreateStripeCustomerIdForUser({
+          prisma,
+          stripe,
+          userId: session.user?.id,
+        });
 
+        if (!customerId) {
+          throw new Error("Could not create customer");
+        }
+
+        const baseUrl =
+          env.NODE_ENV === "development"
+            ? `http://${req.headers.host ?? "localhost:3000"}`
+            : `https://${req.headers.host ?? env.NEXTAUTH_URL}`;
+
+        const checkoutSession = await stripe.checkout.sessions.create({
+          customer: customerId,
+          client_reference_id: session.user?.id,
+          payment_method_types: ["card"],
+          allow_promotion_codes: true,
+          mode: "subscription",
+          line_items: [
+            {
+              price: input.billedAnnually
+                ? env.STRIPE_ANNUAL_PRICE_ID
+                : env.STRIPE_MONTHLY_PRICE_ID,
+              quantity: 1,
+            },
+          ],
+          success_url: `${baseUrl}/videos?checkoutSuccess=true`,
+          cancel_url: `${baseUrl}/videos?checkoutCanceled=true`,
+          subscription_data: {
+            metadata: {
+              userId: session.user?.id,
+            },
+          },
+        });
+
+        if (!checkoutSession) {
+          throw new Error("Could not create checkout session");
+        }
+
+        posthog.capture({
+          distinctId: session.user.id,
+          event: "visiting checkout page",
+          properties: {
+            billingCycle: input.billedAnnually ? "annual" : "monthly",
+          },
+        });
+        void posthog.shutdownAsync();
+
+        return { checkoutUrl: checkoutSession.url };
+      }
+    ),
+  createBillingPortalSession: protectedProcedure.mutation(
+    async ({ ctx: { stripe, session, prisma, req, posthog } }) => {
       const customerId = await getOrCreateStripeCustomerIdForUser({
         prisma,
         stripe,
@@ -24,63 +79,26 @@ export const stripeRouter = createTRPCRouter({
           ? `http://${req.headers.host ?? "localhost:3000"}`
           : `https://${req.headers.host ?? env.NEXTAUTH_URL}`;
 
-      const checkoutSession = await stripe.checkout.sessions.create({
-        customer: customerId,
-        client_reference_id: session.user?.id,
-        payment_method_types: ["card"],
-        allow_promotion_codes: true,
-        mode: "subscription",
-        line_items: [
-          {
-            price: input.billedAnnually
-              ? env.STRIPE_ANNUAL_PRICE_ID
-              : env.STRIPE_MONTHLY_PRICE_ID,
-            quantity: 1,
-          },
-        ],
-        success_url: `${baseUrl}/videos?checkoutSuccess=true`,
-        cancel_url: `${baseUrl}/videos?checkoutCanceled=true`,
-        subscription_data: {
-          metadata: {
-            userId: session.user?.id,
-          },
-        },
-      });
+      const stripeBillingPortalSession =
+        await stripe.billingPortal.sessions.create({
+          customer: customerId,
+          return_url: `${baseUrl}/videos`,
+        });
 
-      if (!checkoutSession) {
-        throw new Error("Could not create checkout session");
+      if (!stripeBillingPortalSession) {
+        throw new Error("Could not create billing portal session");
       }
 
-      return { checkoutUrl: checkoutSession.url };
-    }),
-  createBillingPortalSession: protectedProcedure.mutation(async ({ ctx }) => {
-    const { stripe, session, prisma, req } = ctx;
-
-    const customerId = await getOrCreateStripeCustomerIdForUser({
-      prisma,
-      stripe,
-      userId: session.user?.id,
-    });
-
-    if (!customerId) {
-      throw new Error("Could not create customer");
-    }
-
-    const baseUrl =
-      env.NODE_ENV === "development"
-        ? `http://${req.headers.host ?? "localhost:3000"}`
-        : `https://${req.headers.host ?? env.NEXTAUTH_URL}`;
-
-    const stripeBillingPortalSession =
-      await stripe.billingPortal.sessions.create({
-        customer: customerId,
-        return_url: `${baseUrl}/videos`,
+      posthog.capture({
+        distinctId: session.user.id,
+        event: "visiting billing portal page",
+        properties: {
+          stripeSubscriptionStatus: session.user.stripeSubscriptionStatus,
+        },
       });
+      void posthog.shutdownAsync();
 
-    if (!stripeBillingPortalSession) {
-      throw new Error("Could not create billing portal session");
+      return { billingPortalUrl: stripeBillingPortalSession.url };
     }
-
-    return { billingPortalUrl: stripeBillingPortalSession.url };
-  }),
+  ),
 });
diff --git a/src/server/api/routers/video.ts b/src/server/api/routers/video.ts
index 7e5ab3f..913f7e2 100644
--- a/src/server/api/routers/video.ts
+++ b/src/server/api/routers/video.ts
@@ -15,34 +15,45 @@ import { getSignedUrl } from "@aws-sdk/s3-request-presigner";
 import { TRPCError } from "@trpc/server";
 
 export const videoRouter = createTRPCRouter({
-  getAll: protectedProcedure.query(async ({ ctx }) => {
-    const videos = await ctx.prisma.video.findMany({
-      where: {
-        userId: ctx.session.user.id,
-      },
-    });
+  getAll: protectedProcedure.query(
+    async ({ ctx: { prisma, session, s3, posthog } }) => {
+      const videos = await prisma.video.findMany({
+        where: {
+          userId: session.user.id,
+        },
+      });
 
-    const videosWithThumbnailUrl = await Promise.all(
-      videos.map(async (video) => {
-        const thumbnailUrl = await getSignedUrl(
-          ctx.s3,
-          new GetObjectCommand({
-            Bucket: env.AWS_BUCKET_NAME,
-            Key: video.userId + "/" + video.id + "-thumbnail",
-          })
-        );
+      posthog.capture({
+        distinctId: session.user.id,
+        event: "viewing video list",
+        properties: {
+          videoAmount: videos.length,
+        },
+      });
+      void posthog.shutdownAsync();
 
-        return { ...video, thumbnailUrl };
-      })
-    );
+      const videosWithThumbnailUrl = await Promise.all(
+        videos.map(async (video) => {
+          const thumbnailUrl = await getSignedUrl(
+            s3,
+            new GetObjectCommand({
+              Bucket: env.AWS_BUCKET_NAME,
+              Key: video.userId + "/" + video.id + "-thumbnail",
+            })
+          );
 
-    return videosWithThumbnailUrl;
-  }),
+          return { ...video, thumbnailUrl };
+        })
+      );
+
+      return videosWithThumbnailUrl;
+    }
+  ),
   get: publicProcedure
     .input(z.object({ videoId: z.string() }))
     .query(async ({ ctx, input }) => {
-      const { s3 } = ctx;
-      const video = await ctx.prisma.video.findUnique({
+      const { s3, posthog, session, prisma } = ctx;
+      const video = await prisma.video.findUnique({
         where: {
           id: input.videoId,
         },
@@ -54,10 +65,27 @@ export const videoRouter = createTRPCRouter({
         throw new TRPCError({ code: "NOT_FOUND" });
       }
 
-      if (video.userId !== ctx?.session?.user.id && !video.sharing) {
+      if (video.userId !== session?.user.id && !video.sharing) {
         throw new TRPCError({ code: "FORBIDDEN" });
       }
 
+      if (session) {
+        posthog.capture({
+          distinctId: session.user.id,
+          event: "viewing video",
+          properties: {
+            videoId: video.id,
+            videoCreatedAt: video.createdAt,
+            videoUpdatedAt: video.updatedAt,
+            videoUser: video.user.id,
+            videoSharing: video.sharing,
+            videoDeleteAfterLinkExpires: video.delete_after_link_expires,
+            videoShareLinkExpiresAt: video.shareLinkExpiresAt,
+          },
+        });
+        void posthog.shutdownAsync();
+      }
+
       const getObjectCommand = new GetObjectCommand({
         Bucket: env.AWS_BUCKET_NAME,
         Key: video.userId + "/" + video.id,
@@ -69,20 +97,29 @@ export const videoRouter = createTRPCRouter({
     }),
   getUploadUrl: protectedProcedure
     .input(z.object({ key: z.string() }))
-    .mutation(async ({ ctx, input }) => {
+    .mutation(async ({ ctx: { prisma, session, s3, posthog }, input }) => {
       const { key } = input;
-      const { s3 } = ctx;
 
-      const videos = await ctx.prisma.video.findMany({
+      const videos = await prisma.video.findMany({
         where: {
-          userId: ctx.session.user.id,
+          userId: session.user.id,
         },
       });
 
       if (
         videos.length >= 10 &&
-        ctx.session.user.stripeSubscriptionStatus !== "active"
+        session.user.stripeSubscriptionStatus !== "active"
       ) {
+        posthog.capture({
+          distinctId: session.user.id,
+          event: "hit video upload limit",
+          properties: {
+            videoAmount: videos.length,
+            stripeSubscriptionStatus: session.user.stripeSubscriptionStatus,
+          },
+        });
+        void posthog.shutdownAsync();
+
         throw new TRPCError({
           code: "FORBIDDEN",
           message:
@@ -90,9 +127,19 @@ export const videoRouter = createTRPCRouter({
         });
       }
 
-      const video = await ctx.prisma.video.create({
+      posthog.capture({
+        distinctId: session.user.id,
+        event: "uploading video",
+        properties: {
+          videoAmount: videos.length,
+          stripeSubscriptionStatus: session.user.stripeSubscriptionStatus,
+        },
+      });
+      void posthog.shutdownAsync();
+
+      const video = await prisma.video.create({
         data: {
-          userId: ctx.session.user.id,
+          userId: session.user.id,
           title: key,
         },
       });
@@ -101,7 +148,7 @@ export const videoRouter = createTRPCRouter({
         s3,
         new PutObjectCommand({
           Bucket: env.AWS_BUCKET_NAME,
-          Key: ctx.session.user.id + "/" + video.id,
+          Key: session.user.id + "/" + video.id,
         })
       );
 
@@ -122,11 +169,11 @@ export const videoRouter = createTRPCRouter({
     }),
   setSharing: protectedProcedure
     .input(z.object({ videoId: z.string(), sharing: z.boolean() }))
-    .mutation(async ({ ctx, input }) => {
-      const updateVideo = await ctx.prisma.video.updateMany({
+    .mutation(async ({ ctx: { prisma, session, posthog }, input }) => {
+      const updateVideo = await prisma.video.updateMany({
         where: {
           id: input.videoId,
-          userId: ctx.session.user.id,
+          userId: session.user.id,
         },
         data: {
           sharing: input.sharing,
@@ -137,6 +184,16 @@ export const videoRouter = createTRPCRouter({
         throw new TRPCError({ code: "FORBIDDEN" });
       }
 
+      posthog.capture({
+        distinctId: session.user.id,
+        event: "update video setSharing",
+        properties: {
+          videoId: input.videoId,
+          videoSharing: input.sharing,
+        },
+      });
+      void posthog.shutdownAsync();
+
       return {
         success: true,
         updateVideo,
@@ -146,11 +203,11 @@ export const videoRouter = createTRPCRouter({
     .input(
       z.object({ videoId: z.string(), delete_after_link_expires: z.boolean() })
     )
-    .mutation(async ({ ctx, input }) => {
-      const updateVideo = await ctx.prisma.video.updateMany({
+    .mutation(async ({ ctx: { prisma, session, posthog }, input }) => {
+      const updateVideo = await prisma.video.updateMany({
         where: {
           id: input.videoId,
-          userId: ctx.session.user.id,
+          userId: session.user.id,
         },
         data: {
           delete_after_link_expires: input.delete_after_link_expires,
@@ -161,6 +218,16 @@ export const videoRouter = createTRPCRouter({
         throw new TRPCError({ code: "FORBIDDEN" });
       }
 
+      posthog.capture({
+        distinctId: session.user.id,
+        event: "update video delete_after_link_expires",
+        properties: {
+          videoId: input.videoId,
+          delete_after_link_expires: input.delete_after_link_expires,
+        },
+      });
+      void posthog.shutdownAsync();
+
       return {
         success: true,
         updateVideo,
@@ -173,11 +240,11 @@ export const videoRouter = createTRPCRouter({
         shareLinkExpiresAt: z.nullable(z.date()),
       })
     )
-    .mutation(async ({ ctx, input }) => {
-      const updateVideo = await ctx.prisma.video.updateMany({
+    .mutation(async ({ ctx: { prisma, session, posthog }, input }) => {
+      const updateVideo = await prisma.video.updateMany({
         where: {
           id: input.videoId,
-          userId: ctx.session.user.id,
+          userId: session.user.id,
         },
         data: {
           shareLinkExpiresAt: input.shareLinkExpiresAt,
@@ -188,6 +255,16 @@ export const videoRouter = createTRPCRouter({
         throw new TRPCError({ code: "FORBIDDEN" });
       }
 
+      posthog.capture({
+        distinctId: session.user.id,
+        event: "update video shareLinkExpiresAt",
+        properties: {
+          videoId: input.videoId,
+          shareLinkExpiresAt: input.shareLinkExpiresAt,
+        },
+      });
+      void posthog.shutdownAsync();
+
       return {
         success: true,
         updateVideo,
@@ -200,11 +277,11 @@ export const videoRouter = createTRPCRouter({
         title: z.string(),
       })
     )
-    .mutation(async ({ ctx, input }) => {
-      const updateVideo = await ctx.prisma.video.updateMany({
+    .mutation(async ({ ctx: { prisma, session, posthog }, input }) => {
+      const updateVideo = await prisma.video.updateMany({
         where: {
           id: input.videoId,
-          userId: ctx.session.user.id,
+          userId: session.user.id,
         },
         data: {
           title: input.title,
@@ -215,6 +292,16 @@ export const videoRouter = createTRPCRouter({
         throw new TRPCError({ code: "FORBIDDEN" });
       }
 
+      posthog.capture({
+        distinctId: session.user.id,
+        event: "update video title",
+        properties: {
+          videoId: input.videoId,
+          title: input.title,
+        },
+      });
+      void posthog.shutdownAsync();
+
       return {
         success: true,
         updateVideo,
@@ -226,11 +313,11 @@ export const videoRouter = createTRPCRouter({
         videoId: z.string(),
       })
     )
-    .mutation(async ({ ctx, input }) => {
-      const deleteVideo = await ctx.prisma.video.deleteMany({
+    .mutation(async ({ ctx: { prisma, session, s3, posthog }, input }) => {
+      const deleteVideo = await prisma.video.deleteMany({
         where: {
           id: input.videoId,
-          userId: ctx.session.user.id,
+          userId: session.user.id,
         },
       });
 
@@ -238,17 +325,26 @@ export const videoRouter = createTRPCRouter({
         throw new TRPCError({ code: "FORBIDDEN" });
       }
 
-      const deleteVideoObject = await ctx.s3.send(
+      posthog.capture({
+        distinctId: session.user.id,
+        event: "video delete",
+        properties: {
+          videoId: input.videoId,
+        },
+      });
+      void posthog.shutdownAsync();
+
+      const deleteVideoObject = await s3.send(
         new DeleteObjectCommand({
           Bucket: env.AWS_BUCKET_NAME,
-          Key: ctx.session.user.id + "/" + input.videoId,
+          Key: session.user.id + "/" + input.videoId,
         })
       );
 
-      const deleteThumbnailObject = await ctx.s3.send(
+      const deleteThumbnailObject = await s3.send(
         new DeleteObjectCommand({
           Bucket: env.AWS_BUCKET_NAME,
-          Key: ctx.session.user.id + "/" + input.videoId + "-thumbnail",
+          Key: session.user.id + "/" + input.videoId + "-thumbnail",
         })
       );
 
diff --git a/src/server/api/trpc.ts b/src/server/api/trpc.ts
index 9224b68..904eb5b 100644
--- a/src/server/api/trpc.ts
+++ b/src/server/api/trpc.ts
@@ -41,6 +41,7 @@ const createInnerTRPCContext = (opts: CreateContextOptions) => {
     session: opts.session,
     prisma,
     s3,
+    posthog,
     stripe,
     req: opts.req,
     res: opts.res,
@@ -79,6 +80,7 @@ import { ZodError } from "zod";
 import { s3 } from "~/server/aws/s3";
 import { stripe } from "~/server/stripe";
 import { type NextApiRequest, type NextApiResponse } from "next";
+import { posthog } from "~/server/posthog";
 
 const t = initTRPC.context<typeof createTRPCContext>().create({
   transformer: superjson,
diff --git a/src/server/auth.ts b/src/server/auth.ts
index d98f7f0..b4e3589 100644
--- a/src/server/auth.ts
+++ b/src/server/auth.ts
@@ -9,6 +9,7 @@ import GitHubProvider from "next-auth/providers/github";
 import { PrismaAdapter } from "@next-auth/prisma-adapter";
 import { env } from "~/env.mjs";
 import { prisma } from "~/server/db";
+import { PostHog } from "posthog-node";
 
 /**
  * Module augmentation for `next-auth` types. Allows us to add custom properties to the `session`
@@ -67,6 +68,44 @@ export const authOptions: NextAuthOptions = {
      * @see https://next-auth.js.org/providers/github
      */
   ],
+  events: {
+    async signIn(message) {
+      const client = new PostHog(env.NEXT_PUBLIC_POSTHOG_KEY, {
+        host: env.NEXT_PUBLIC_POSTHOG_HOST,
+      });
+
+      client.capture({
+        distinctId: message.user.id,
+        event: "user logged in",
+        properties: {
+          provider: message.account?.provider,
+          isNewUser: message.isNewUser,
+        },
+      });
+
+      await client.shutdownAsync();
+    },
+    async signOut(message) {
+      const session = message.session as unknown as {
+        id: string;
+        sessionToken: string;
+        userId: string;
+        expires: Date;
+      };
+      if (!session?.userId) return;
+
+      const client = new PostHog(env.NEXT_PUBLIC_POSTHOG_KEY, {
+        host: env.NEXT_PUBLIC_POSTHOG_HOST,
+      });
+
+      client.capture({
+        distinctId: session.userId,
+        event: "user logged out",
+      });
+
+      await client.shutdownAsync();
+    },
+  },
   pages: {
     signIn: "/sign-in",
   },
diff --git a/src/server/posthog.ts b/src/server/posthog.ts
new file mode 100644
index 0000000..1c9869e
--- /dev/null
+++ b/src/server/posthog.ts
@@ -0,0 +1,6 @@
+import { PostHog } from "posthog-node";
+import { env } from "~/env.mjs";
+
+export const posthog = new PostHog(env.NEXT_PUBLIC_POSTHOG_KEY, {
+  host: env.NEXT_PUBLIC_POSTHOG_HOST,
+});
diff --git a/src/server/stripe-webhook-handlers.ts b/src/server/stripe-webhook-handlers.ts
index aae52ba..397adf6 100644
--- a/src/server/stripe-webhook-handlers.ts
+++ b/src/server/stripe-webhook-handlers.ts
@@ -1,5 +1,6 @@
 import type { PrismaClient } from "@prisma/client";
 import type Stripe from "stripe";
+import { type PostHog } from "posthog-node";
 
 // retrieves a Stripe customer id for a given user if it exists or creates a new one
 export const getOrCreateStripeCustomerIdForUser = async ({
@@ -54,10 +55,12 @@ export const handleInvoicePaid = async ({
   event,
   stripe,
   prisma,
+  posthog,
 }: {
   event: Stripe.Event;
   stripe: Stripe;
   prisma: PrismaClient;
+  posthog: PostHog;
 }) => {
   const invoice = event.data.object as Stripe.Invoice;
   const subscriptionId = invoice.subscription;
@@ -76,14 +79,27 @@ export const handleInvoicePaid = async ({
       stripeSubscriptionStatus: subscription.status,
     },
   });
+
+  if (userId && subscription.status) {
+    posthog.capture({
+      distinctId: userId,
+      event: "stripe invoice.paid",
+      properties: {
+        stripeSubscriptionStatus: subscription.status,
+      },
+    });
+    void posthog.shutdownAsync();
+  }
 };
 
 export const handleSubscriptionCreatedOrUpdated = async ({
   event,
   prisma,
+  posthog,
 }: {
   event: Stripe.Event;
   prisma: PrismaClient;
+  posthog: PostHog;
 }) => {
   const subscription = event.data.object as Stripe.Subscription;
   const userId = subscription.metadata.userId;
@@ -98,14 +114,24 @@ export const handleSubscriptionCreatedOrUpdated = async ({
       stripeSubscriptionStatus: subscription.status,
     },
   });
+
+  if (userId && subscription.status) {
+    posthog.capture({
+      distinctId: userId,
+      event: "stripe subscription created or updated",
+    });
+    void posthog.shutdownAsync();
+  }
 };
 
 export const handleSubscriptionCanceled = async ({
   event,
   prisma,
+  posthog,
 }: {
   event: Stripe.Event;
   prisma: PrismaClient;
+  posthog: PostHog;
 }) => {
   const subscription = event.data.object as Stripe.Subscription;
   const userId = subscription.metadata.userId;
@@ -120,4 +146,12 @@ export const handleSubscriptionCanceled = async ({
       stripeSubscriptionStatus: null,
     },
   });
+
+  if (userId && subscription.status) {
+    posthog.capture({
+      distinctId: userId,
+      event: "stripe subscription cancelled",
+    });
+    void posthog.shutdownAsync();
+  }
 };