diff --git a/apps/dashboard/src/app/(dashboard)/monitors/(list)/nav-actions.tsx b/apps/dashboard/src/app/(dashboard)/monitors/(list)/nav-actions.tsx
index dc20300a9..2eb0fefcc 100644
--- a/apps/dashboard/src/app/(dashboard)/monitors/(list)/nav-actions.tsx
+++ b/apps/dashboard/src/app/(dashboard)/monitors/(list)/nav-actions.tsx
@@ -24,6 +24,8 @@ export function NavActions() {
       <NavFeedback />
       {limitReached ? (
         <Button
+          data-track="paywall_viewed"
+          data-limit="monitors"
           size="sm"
           data-limited={limitReached}
           className="data-[limited=true]:opacity-80"
diff --git a/apps/dashboard/src/app/(dashboard)/monitors/[id]/logs/client.tsx b/apps/dashboard/src/app/(dashboard)/monitors/[id]/logs/client.tsx
index 8808a5fb3..199d7ce18 100644
--- a/apps/dashboard/src/app/(dashboard)/monitors/[id]/logs/client.tsx
+++ b/apps/dashboard/src/app/(dashboard)/monitors/[id]/logs/client.tsx
@@ -389,7 +389,11 @@ function BillingPlaceholder() {
         />
       </DataTableStoreProvider>
       <BillingOverlay>
-        <BillingOverlayButton asChild>
+        <BillingOverlayButton
+          data-track="paywall_viewed"
+          data-limit="response-logs"
+          asChild
+        >
           <Link href="/settings/billing">
             <Lock />
             Upgrade
diff --git a/apps/dashboard/src/app/(dashboard)/settings/audit-logs/client.tsx b/apps/dashboard/src/app/(dashboard)/settings/audit-logs/client.tsx
index 577306549..965734b4f 100644
--- a/apps/dashboard/src/app/(dashboard)/settings/audit-logs/client.tsx
+++ b/apps/dashboard/src/app/(dashboard)/settings/audit-logs/client.tsx
@@ -130,7 +130,11 @@ export function Client() {
               )}
             />
             <BillingOverlay>
-              <BillingOverlayButton onClick={() => setOpenDialog(true)}>
+              <BillingOverlayButton
+                data-track="paywall_viewed"
+                data-limit="audit-log"
+                onClick={() => setOpenDialog(true)}
+              >
                 <Lock />
                 Upgrade
               </BillingOverlayButton>
diff --git a/apps/dashboard/src/app/(dashboard)/settings/integrations/slack-card.tsx b/apps/dashboard/src/app/(dashboard)/settings/integrations/slack-card.tsx
index 0f4d3e443..6d9e7a941 100644
--- a/apps/dashboard/src/app/(dashboard)/settings/integrations/slack-card.tsx
+++ b/apps/dashboard/src/app/(dashboard)/settings/integrations/slack-card.tsx
@@ -160,7 +160,12 @@ export function SlackIntegrationCard({
           .
         </FormCardFooterInfo>
         {locked ? (
-          <Button type="button" asChild>
+          <Button
+            data-track="paywall_viewed"
+            data-limit="slack-agent"
+            type="button"
+            asChild
+          >
             <Link href="/settings/billing">
               <Lock />
               Upgrade
diff --git a/apps/dashboard/src/app/(dashboard)/settings/private-locations/client.tsx b/apps/dashboard/src/app/(dashboard)/settings/private-locations/client.tsx
index 86d4a57c3..bb993d46b 100644
--- a/apps/dashboard/src/app/(dashboard)/settings/private-locations/client.tsx
+++ b/apps/dashboard/src/app/(dashboard)/settings/private-locations/client.tsx
@@ -78,7 +78,11 @@ export function Client() {
               data={[...EXAMPLES, ...EXAMPLES, ...EXAMPLES]}
             />
             <BillingOverlay>
-              <BillingOverlayButton onClick={() => setOpenDialog(true)}>
+              <BillingOverlayButton
+                data-track="paywall_viewed"
+                data-limit="private-locations"
+                onClick={() => setOpenDialog(true)}
+              >
                 <Lock />
                 Upgrade
               </BillingOverlayButton>
diff --git a/apps/dashboard/src/app/(dashboard)/settings/private-locations/nav-actions.tsx b/apps/dashboard/src/app/(dashboard)/settings/private-locations/nav-actions.tsx
index f68f0a309..015cec18a 100644
--- a/apps/dashboard/src/app/(dashboard)/settings/private-locations/nav-actions.tsx
+++ b/apps/dashboard/src/app/(dashboard)/settings/private-locations/nav-actions.tsx
@@ -34,6 +34,8 @@ export function NavActions() {
       <NavFeedback />
       {limitReached ? (
         <Button
+          data-track="paywall_viewed"
+          data-limit="private-locations"
           size="sm"
           data-disabled={limitReached}
           className="data-[disabled=true]:opacity-50"
diff --git a/apps/dashboard/src/app/(dashboard)/settings/sso/page.tsx b/apps/dashboard/src/app/(dashboard)/settings/sso/page.tsx
index a1bd5c4f8..2526783be 100644
--- a/apps/dashboard/src/app/(dashboard)/settings/sso/page.tsx
+++ b/apps/dashboard/src/app/(dashboard)/settings/sso/page.tsx
@@ -148,7 +148,12 @@ export default function Page() {
                     ? "Add it to connect Okta, Entra ID, or any SAML provider."
                     : "Upgrade to connect Okta, Entra ID, or any SAML provider."}
                 </FormCardFooterInfo>
-                <Button size="sm" onClick={() => setUpgradeOpen(true)}>
+                <Button
+                  data-track="paywall_viewed"
+                  data-limit="sso"
+                  size="sm"
+                  onClick={() => setUpgradeOpen(true)}
+                >
                   {ssoAddon ? "Add SSO" : "Upgrade"}
                 </Button>
               </FormCardFooter>
diff --git a/apps/dashboard/src/app/(dashboard)/status-pages/(list)/nav-actions.tsx b/apps/dashboard/src/app/(dashboard)/status-pages/(list)/nav-actions.tsx
index d13779c0d..cb2987d1e 100644
--- a/apps/dashboard/src/app/(dashboard)/status-pages/(list)/nav-actions.tsx
+++ b/apps/dashboard/src/app/(dashboard)/status-pages/(list)/nav-actions.tsx
@@ -24,6 +24,8 @@ export function NavActions() {
       <NavFeedback />
       {limitReached ? (
         <Button
+          data-track="paywall_viewed"
+          data-limit="status-pages"
           size="sm"
           data-limited={limitReached}
           className="data-[limited=true]:opacity-80"
diff --git a/apps/dashboard/src/app/(dashboard)/status-pages/[id]/history/client.tsx b/apps/dashboard/src/app/(dashboard)/status-pages/[id]/history/client.tsx
index 1904d78b0..bbf4188fe 100644
--- a/apps/dashboard/src/app/(dashboard)/status-pages/[id]/history/client.tsx
+++ b/apps/dashboard/src/app/(dashboard)/status-pages/[id]/history/client.tsx
@@ -169,7 +169,11 @@ export function Client() {
               />
             </div>
             <BillingOverlay>
-              <BillingOverlayButton onClick={() => setOpenDialog(true)}>
+              <BillingOverlayButton
+                data-track="paywall_viewed"
+                data-limit="uptime-history"
+                onClick={() => setOpenDialog(true)}
+              >
                 <Lock />
                 Upgrade
               </BillingOverlayButton>
diff --git a/apps/dashboard/src/app/(dashboard)/status-pages/[id]/subscribers/page.tsx b/apps/dashboard/src/app/(dashboard)/status-pages/[id]/subscribers/page.tsx
index dc6fcca18..16125fe5d 100644
--- a/apps/dashboard/src/app/(dashboard)/status-pages/[id]/subscribers/page.tsx
+++ b/apps/dashboard/src/app/(dashboard)/status-pages/[id]/subscribers/page.tsx
@@ -112,6 +112,8 @@ export default function Page() {
           <div>
             {isLimited ? (
               <Button
+                data-track="paywall_viewed"
+                data-limit="status-subscribers"
                 variant="outline"
                 size="sm"
                 onClick={() => setOpenDialog(true)}
@@ -161,7 +163,11 @@ export default function Page() {
               data={[...EXAMPLES, ...EXAMPLES, ...EXAMPLES]}
             />
             <BillingOverlay>
-              <BillingOverlayButton onClick={() => setOpenDialog(true)}>
+              <BillingOverlayButton
+                data-track="paywall_viewed"
+                data-limit="status-subscribers"
+                onClick={() => setOpenDialog(true)}
+              >
                 <Lock />
                 Upgrade
               </BillingOverlayButton>
diff --git a/apps/dashboard/src/app/layout.tsx b/apps/dashboard/src/app/layout.tsx
index df18a14d1..069089ffb 100644
--- a/apps/dashboard/src/app/layout.tsx
+++ b/apps/dashboard/src/app/layout.tsx
@@ -109,10 +109,12 @@ export default async function RootLayout({
                 {process.env.NEXT_PUBLIC_OPENPANEL_CLIENT_ID && (
                   <OpenPanelComponent
                     clientId={process.env.NEXT_PUBLIC_OPENPANEL_CLIENT_ID}
+                    profileId={
+                      session?.user?.id ? `usr_${session.user.id}` : undefined
+                    }
                     trackScreenViews
                     trackOutgoingLinks
                     trackAttributes
-                    sessionReplay={{ enabled: true }}
                   />
                 )}
               </ThemeProvider>
diff --git a/apps/dashboard/src/components/controls-search/command-region.tsx b/apps/dashboard/src/components/controls-search/command-region.tsx
index 5b0805c8c..b2ff3ab99 100644
--- a/apps/dashboard/src/components/controls-search/command-region.tsx
+++ b/apps/dashboard/src/components/controls-search/command-region.tsx
@@ -204,7 +204,11 @@ export function CommandRegion({
         </Command>
         {limited ? (
           <BillingOverlay className="to-70%">
-            <BillingOverlayButton asChild>
+            <BillingOverlayButton
+              data-track="paywall_viewed"
+              data-limit="max-regions"
+              asChild
+            >
               <Link href="/settings/billing">
                 <Lock />
                 Upgrade
diff --git a/apps/dashboard/src/components/forms/monitor/form-otel.tsx b/apps/dashboard/src/components/forms/monitor/form-otel.tsx
index fad3f244e..f6dc8b669 100644
--- a/apps/dashboard/src/components/forms/monitor/form-otel.tsx
+++ b/apps/dashboard/src/components/forms/monitor/form-otel.tsx
@@ -183,7 +183,7 @@ export function FormOtel({
               .
             </FormCardFooterInfo>
             {locked ? (
-              <Button asChild>
+              <Button data-track="paywall_viewed" data-limit="otel" asChild>
                 <NextLink href="/settings/billing">
                   <Lock className="size-4" />
                   Upgrade
diff --git a/apps/dashboard/src/components/forms/monitor/form-scheduling-regions.tsx b/apps/dashboard/src/components/forms/monitor/form-scheduling-regions.tsx
index df06bf1b9..38b3698a6 100644
--- a/apps/dashboard/src/components/forms/monitor/form-scheduling-regions.tsx
+++ b/apps/dashboard/src/components/forms/monitor/form-scheduling-regions.tsx
@@ -188,7 +188,12 @@ export function FormSchedulingRegions({
               <Note color="error">
                 <Error />
                 The periodicity you are selecting is not allowed for your plan.
-                <NoteButton type="button" onClick={() => setOpenDialog(true)}>
+                <NoteButton
+                  data-track="paywall_viewed"
+                  data-limit="periodicity"
+                  type="button"
+                  onClick={() => setOpenDialog(true)}
+                >
                   Upgrade your plan
                 </NoteButton>
               </Note>
diff --git a/apps/dashboard/src/components/forms/monitor/form-visibility.tsx b/apps/dashboard/src/components/forms/monitor/form-visibility.tsx
index 31e7bb6e1..2b831c185 100644
--- a/apps/dashboard/src/components/forms/monitor/form-visibility.tsx
+++ b/apps/dashboard/src/components/forms/monitor/form-visibility.tsx
@@ -121,7 +121,11 @@ export function FormVisibility({
               .
             </FormCardFooterInfo>
             {locked ? (
-              <Button asChild>
+              <Button
+                data-track="paywall_viewed"
+                data-limit="monitor-values-visibility"
+                asChild
+              >
                 <NextLink href="/settings/billing">
                   <Lock className="size-4" />
                   Upgrade
diff --git a/apps/dashboard/src/components/forms/settings/form-members.tsx b/apps/dashboard/src/components/forms/settings/form-members.tsx
index cd0cbec79..e4598300a 100644
--- a/apps/dashboard/src/components/forms/settings/form-members.tsx
+++ b/apps/dashboard/src/components/forms/settings/form-members.tsx
@@ -142,7 +142,13 @@ export function FormMembers({
                   </Link>
                   .
                 </FormCardFooterInfo>
-                <Button type="button" size="sm" asChild>
+                <Button
+                  data-track="paywall_viewed"
+                  data-limit="members"
+                  type="button"
+                  size="sm"
+                  asChild
+                >
                   <Link href="/settings/billing">
                     <Lock />
                     Upgrade
diff --git a/apps/dashboard/src/components/forms/status-page/form-custom-domain.tsx b/apps/dashboard/src/components/forms/status-page/form-custom-domain.tsx
index d1f47b6a1..bda3b4e6d 100644
--- a/apps/dashboard/src/components/forms/status-page/form-custom-domain.tsx
+++ b/apps/dashboard/src/components/forms/status-page/form-custom-domain.tsx
@@ -145,7 +145,12 @@ export function FormCustomDomain({
               .
             </FormCardFooterInfo>
             {locked ? (
-              <Button type="button" asChild>
+              <Button
+                data-track="paywall_viewed"
+                data-limit="custom-domain"
+                type="button"
+                asChild
+              >
                 <Link href="/settings/billing">
                   <Lock />
                   Upgrade
diff --git a/apps/dashboard/src/components/forms/status-page/form-custom-theme.tsx b/apps/dashboard/src/components/forms/status-page/form-custom-theme.tsx
index c0b1cd694..8933793d3 100644
--- a/apps/dashboard/src/components/forms/status-page/form-custom-theme.tsx
+++ b/apps/dashboard/src/components/forms/status-page/form-custom-theme.tsx
@@ -197,7 +197,12 @@ export function FormCustomTheme({
               .
             </FormCardFooterInfo>
             {locked ? (
-              <Button type="button" asChild>
+              <Button
+                data-track="paywall_viewed"
+                data-limit="custom-theme"
+                type="button"
+                asChild
+              >
                 <Link href="/settings/billing">
                   <Lock className="size-4" />
                   Upgrade
diff --git a/apps/dashboard/src/components/forms/status-page/form-locale.tsx b/apps/dashboard/src/components/forms/status-page/form-locale.tsx
index 9be136e94..41723ee49 100644
--- a/apps/dashboard/src/components/forms/status-page/form-locale.tsx
+++ b/apps/dashboard/src/components/forms/status-page/form-locale.tsx
@@ -229,7 +229,12 @@ export function FormLocale({
               .
             </FormCardFooterInfo>
             {locked ? (
-              <Button type="button" asChild>
+              <Button
+                data-track="paywall_viewed"
+                data-limit="i18n"
+                type="button"
+                asChild
+              >
                 <Link href="/settings/billing">
                   <Lock className="size-4" />
                   Upgrade
diff --git a/apps/dashboard/src/components/forms/status-page/form-page-access.tsx b/apps/dashboard/src/components/forms/status-page/form-page-access.tsx
index c723f3b8b..51a8adce9 100644
--- a/apps/dashboard/src/components/forms/status-page/form-page-access.tsx
+++ b/apps/dashboard/src/components/forms/status-page/form-page-access.tsx
@@ -1,6 +1,7 @@
 "use client";
 
 import { zodResolver } from "@hookform/resolvers/zod";
+import type { Limits } from "@openstatus/db/src/schema/plan/schema";
 import {
   ApiKey,
   Lock,
@@ -88,6 +89,13 @@ const schema = z.object({
 
 type FormValues = z.infer<typeof schema>;
 
+const ACCESS_TYPE_LIMIT = {
+  public: undefined,
+  password: "password-protection",
+  "email-domain": "email-domain-protection",
+  "ip-restriction": "ip-restriction",
+} satisfies Record<z.infer<typeof accessTypeSchema>, keyof Limits | undefined>;
+
 export function FormPageAccess({
   lockedMap,
   allowIndexLocked,
@@ -325,7 +333,12 @@ export function FormPageAccess({
               .
             </FormCardFooterInfo>
             {locked ? (
-              <Button type="button" asChild>
+              <Button
+                data-track="paywall_viewed"
+                data-limit={ACCESS_TYPE_LIMIT[watchAccessType]}
+                type="button"
+                asChild
+              >
                 <Link href="/settings/billing">
                   <Lock />
                   Upgrade
diff --git a/apps/dashboard/src/components/nav/nav-monitors.tsx b/apps/dashboard/src/components/nav/nav-monitors.tsx
index cea0b00b9..ad80e2bb6 100644
--- a/apps/dashboard/src/components/nav/nav-monitors.tsx
+++ b/apps/dashboard/src/components/nav/nav-monitors.tsx
@@ -102,6 +102,8 @@ export function NavMonitors() {
               <TooltipTrigger asChild>
                 <SidebarMenuAction
                   data-limited={limitReached}
+                  data-track={limitReached ? "paywall_viewed" : undefined}
+                  data-limit={limitReached ? "monitors" : undefined}
                   className="relative top-0 right-0 border data-[limited=true]:opacity-80"
                   onClick={() => {
                     if (limitReached) {
diff --git a/apps/dashboard/src/components/nav/nav-status-pages.tsx b/apps/dashboard/src/components/nav/nav-status-pages.tsx
index 68ac1bda0..f55891a91 100644
--- a/apps/dashboard/src/components/nav/nav-status-pages.tsx
+++ b/apps/dashboard/src/components/nav/nav-status-pages.tsx
@@ -83,6 +83,8 @@ export function NavStatusPages() {
               <TooltipTrigger asChild>
                 <SidebarMenuAction
                   data-limited={limitReached}
+                  data-track={limitReached ? "paywall_viewed" : undefined}
+                  data-limit={limitReached ? "status-pages" : undefined}
                   className="relative top-0 right-0 border data-[limited=true]:opacity-80"
                   onClick={() => {
                     if (limitReached) {
diff --git a/apps/dashboard/src/lib/auth/index.ts b/apps/dashboard/src/lib/auth/index.ts
index da98a158f..0238d40b1 100644
--- a/apps/dashboard/src/lib/auth/index.ts
+++ b/apps/dashboard/src/lib/auth/index.ts
@@ -95,9 +95,10 @@ async function onNewUser(
     email: newUser.email,
     location: requestHeaders.get("x-forwarded-for") ?? undefined,
     userAgent: requestHeaders.get("user-agent") ?? undefined,
+    source: "dashboard",
   });
 
-  await analytics.track(Events.CreateUser);
+  await analytics.track({ ...Events.CreateUser, provider });
   if (trial.started) {
     await analytics.track({ ...Events.StartTrial, currency });
   } else if (trial.reason !== "disabled") {
@@ -233,9 +234,13 @@ const {
         email: params.user.email,
         location: (await headers()).get("x-forwarded-for") ?? undefined,
         userAgent: (await headers()).get("user-agent") ?? undefined,
+        source: "dashboard",
       });
 
-      await analytics.track(Events.SignInUser);
+      await analytics.track({
+        ...Events.SignInUser,
+        provider: params.account?.provider,
+      });
     },
   },
   pages: {
diff --git a/apps/server/src/libs/middlewares/track.ts b/apps/server/src/libs/middlewares/track.ts
index 2d882cf78..946aea3da 100644
--- a/apps/server/src/libs/middlewares/track.ts
+++ b/apps/server/src/libs/middlewares/track.ts
@@ -33,11 +33,13 @@ export function trackMiddleware(event: EventProps, eventProps?: string[]) {
       setupAnalytics({
         userId: `api_${workspace.id}`,
         workspaceId: `${workspace.id}`,
+        workspaceName: workspace.name || workspace.slug,
         plan: workspace.plan,
+        source: "api",
         location: c.req.raw.headers.get("x-forwarded-for") ?? undefined,
         userAgent: c.req.raw.headers.get("user-agent") ?? undefined,
       })
-        .then((analytics) => analytics.track({ ...event, additionalProps }))
+        .then((analytics) => analytics.track({ ...additionalProps, ...event }))
         .catch(() => {
           logger.warn(
             "Failed to send analytics event {event} for workspace {workspaceId}",
diff --git a/apps/server/src/routes/mcp/handler.test.ts b/apps/server/src/routes/mcp/handler.test.ts
index 121f4b4be..c47cc5e45 100644
--- a/apps/server/src/routes/mcp/handler.test.ts
+++ b/apps/server/src/routes/mcp/handler.test.ts
@@ -281,6 +281,8 @@ describe("MCP transport — analytics", () => {
       unknown
     >;
     expect(identify?.userId).toBe(`api_${SEEDED_WORKSPACE_TEAM_ID}`);
+    expect(identify?.workspaceId).toBe(`${SEEDED_WORKSPACE_TEAM_ID}`);
+    expect(identify?.source).toBe("mcp");
 
     const event = analyticsSpies.track.mock.calls[0]?.[0] as Record<
       string,
diff --git a/apps/server/src/routes/mcp/index.ts b/apps/server/src/routes/mcp/index.ts
index f8104a88a..47dd6f276 100644
--- a/apps/server/src/routes/mcp/index.ts
+++ b/apps/server/src/routes/mcp/index.ts
@@ -88,7 +88,9 @@ function trackMcpRequest(
   setupAnalytics({
     userId: `api_${workspace.id}`,
     workspaceId: `${workspace.id}`,
+    workspaceName: workspace.name || workspace.slug,
     plan: workspace.plan,
+    source: "mcp",
     location: c.req.header("x-forwarded-for"),
     userAgent: c.req.header("user-agent"),
   })
diff --git a/apps/server/src/routes/rpc/interceptors/__tests__/tracking.test.ts b/apps/server/src/routes/rpc/interceptors/__tests__/tracking.test.ts
index e9bc20686..bcda25990 100644
--- a/apps/server/src/routes/rpc/interceptors/__tests__/tracking.test.ts
+++ b/apps/server/src/routes/rpc/interceptors/__tests__/tracking.test.ts
@@ -101,7 +101,9 @@ describe("trackingInterceptor", () => {
     expect(mockSetupAnalytics).toHaveBeenCalledWith({
       userId: "api_42",
       workspaceId: "42",
+      workspaceName: "test-ws",
       plan: "free",
+      source: "api",
       location: "1.2.3.4",
       userAgent: "test-agent",
     });
@@ -112,7 +114,6 @@ describe("trackingInterceptor", () => {
     expect(mockTrack).toHaveBeenCalledTimes(1);
     expect(mockTrack).toHaveBeenCalledWith({
       ...Events.DeleteMonitor,
-      additionalProps: {},
     });
   });
 
@@ -130,7 +131,8 @@ describe("trackingInterceptor", () => {
 
     expect(mockTrack).toHaveBeenCalledWith({
       ...Events.CreateMonitor,
-      additionalProps: { url: "https://example.com", jobType: "http" },
+      url: "https://example.com",
+      jobType: "http",
     });
   });
 
@@ -148,7 +150,8 @@ describe("trackingInterceptor", () => {
 
     expect(mockTrack).toHaveBeenCalledWith({
       ...Events.CreateMonitor,
-      additionalProps: { url: "example.com", jobType: "icmp" },
+      url: "example.com",
+      jobType: "icmp",
     });
   });
 
@@ -230,7 +233,9 @@ describe("trackingInterceptor", () => {
     expect(mockSetupAnalytics).toHaveBeenCalledWith({
       userId: "api_42",
       workspaceId: "42",
+      workspaceName: "test-ws",
       plan: "free",
+      source: "api",
       location: "1.2.3.4",
       userAgent: "test-agent",
     });
@@ -240,7 +245,7 @@ describe("trackingInterceptor", () => {
 
     expect(mockTrack).toHaveBeenCalledWith({
       ...Events.CreateNotification,
-      additionalProps: { provider: "slack" },
+      provider: "slack",
     });
   });
 });
diff --git a/apps/server/src/routes/rpc/interceptors/tracking.ts b/apps/server/src/routes/rpc/interceptors/tracking.ts
index 57cdae602..0511bf96e 100644
--- a/apps/server/src/routes/rpc/interceptors/tracking.ts
+++ b/apps/server/src/routes/rpc/interceptors/tracking.ts
@@ -178,12 +178,14 @@ export function trackingInterceptor(): Interceptor {
     setupAnalytics({
       userId: `api_${rpcCtx.workspace.id}`,
       workspaceId: `${rpcCtx.workspace.id}`,
+      workspaceName: rpcCtx.workspace.name || rpcCtx.workspace.slug,
       plan: rpcCtx.workspace.plan,
+      source: "api",
       location: req.header.get("x-forwarded-for") ?? undefined,
       userAgent: req.header.get("user-agent") ?? undefined,
     })
       .then((analytics) =>
-        analytics.track({ ...mapping.event, additionalProps }),
+        analytics.track({ ...additionalProps, ...mapping.event }),
       )
       .catch(() => {
         logger.warn(
diff --git a/apps/server/src/routes/slack/incident-analytics.ts b/apps/server/src/routes/slack/incident-analytics.ts
index 6312eb80d..e8629a16f 100644
--- a/apps/server/src/routes/slack/incident-analytics.ts
+++ b/apps/server/src/routes/slack/incident-analytics.ts
@@ -18,12 +18,12 @@ export function trackSlackIncident(
 ): void {
   const userId = tryGetActorUserId(ctx.actor);
   setupAnalytics({
-    userId: userId ? `usr_${userId}` : `slack_${ctx.workspace.id}`,
+    userId: userId ? `usr_${userId}` : undefined,
     workspaceId: String(ctx.workspace.id),
+    workspaceName: ctx.workspace.name || ctx.workspace.slug,
     plan: ctx.workspace.plan,
+    source: "slack",
   })
-    .then((analytics) =>
-      analytics.track({ ...EVENTS[kind], source: "slack", ...props }),
-    )
+    .then((analytics) => analytics.track({ ...props, ...EVENTS[kind] }))
     .catch(() => undefined);
 }
diff --git a/apps/server/src/routes/slack/oauth.ts b/apps/server/src/routes/slack/oauth.ts
index d413b8326..affed3118 100644
--- a/apps/server/src/routes/slack/oauth.ts
+++ b/apps/server/src/routes/slack/oauth.ts
@@ -1,6 +1,7 @@
 import crypto from "node:crypto";
 
 import { getLogger } from "@logtape/logtape";
+import { Events, setupAnalytics } from "@openstatus/analytics";
 import { db, eq } from "@openstatus/db";
 import {
   selectWorkspaceSchema,
@@ -179,6 +180,16 @@ export async function handleSlackOAuthCallback(c: Context<SlackEnv>) {
     );
   }
 
+  setupAnalytics({
+    userId: `usr_${state.userId}`,
+    workspaceId: String(workspaceParsed.data.id),
+    workspaceName: workspaceParsed.data.name || workspaceParsed.data.slug,
+    plan: workspaceParsed.data.plan,
+    source: "slack",
+  })
+    .then((analytics) => analytics.track(Events.InstallSlackAgent))
+    .catch(() => undefined);
+
   return c.redirect(
     `${config.dashboardUrl}/settings/integrations?slack=success`,
   );
diff --git a/apps/web/src/app/(landing)/play/cdn-checker/api/route.ts b/apps/web/src/app/(landing)/play/cdn-checker/api/route.ts
index d529001cb..68c594d47 100644
--- a/apps/web/src/app/(landing)/play/cdn-checker/api/route.ts
+++ b/apps/web/src/app/(landing)/play/cdn-checker/api/route.ts
@@ -122,7 +122,7 @@ export async function POST(request: Request) {
 
   after(async () => {
     try {
-      const analytics = await setupAnalytics({});
+      const analytics = await setupAnalytics({ source: "web" });
       await analytics.track({
         ...Events.CdnChecker,
         url: urlForAnalytics(parsed.url),
diff --git a/apps/web/src/app/(landing)/play/checker/api/route.ts b/apps/web/src/app/(landing)/play/checker/api/route.ts
index 13ba62af3..e56d05932 100644
--- a/apps/web/src/app/(landing)/play/checker/api/route.ts
+++ b/apps/web/src/app/(landing)/play/checker/api/route.ts
@@ -247,7 +247,7 @@ export async function POST(request: Request) {
   const compact = new URL(request.url).searchParams.get("compact") === "true";
   const uuid = crypto.randomUUID().replace(/-/g, "");
   after(async () => {
-    const analytics = await setupAnalytics({});
+    const analytics = await setupAnalytics({ source: "web" });
     const additionalProps = { url, uuid, compact };
     await analytics.track({ ...Events.GlobalSpeedChecker, ...additionalProps });
   });
diff --git a/apps/web/src/app/(landing)/play/mcp-health/api/route.ts b/apps/web/src/app/(landing)/play/mcp-health/api/route.ts
index 1332df096..5be3af23d 100644
--- a/apps/web/src/app/(landing)/play/mcp-health/api/route.ts
+++ b/apps/web/src/app/(landing)/play/mcp-health/api/route.ts
@@ -167,7 +167,7 @@ export async function POST(request: Request) {
       console.error("mcp-health redis store failed", error);
     }
     try {
-      const analytics = await setupAnalytics({});
+      const analytics = await setupAnalytics({ source: "web" });
       await analytics.track({
         ...Events.MCPHealthCheck,
         url: normalizeUrlForStorage(parsed.url),
diff --git a/packages/analytics/src/events.ts b/packages/analytics/src/events.ts
index 65aeafa07..074065184 100644
--- a/packages/analytics/src/events.ts
+++ b/packages/analytics/src/events.ts
@@ -132,6 +132,10 @@ export const Events = {
     name: "notification_updated",
     channel: "notification",
   },
+  TestNotification: {
+    name: "notification_tested",
+    channel: "notification",
+  },
   DeleteNotification: {
     name: "notification_deleted",
     channel: "notification",
@@ -256,6 +260,46 @@ export const Events = {
     name: "trial_converted",
     channel: "billing",
   },
+  AddTrialPaymentMethod: {
+    name: "trial_payment_method_added",
+    channel: "billing",
+  },
+  NotifyTrialEnding: {
+    name: "trial_ending_notified",
+    channel: "billing",
+  },
+  ExpireTrial: {
+    name: "trial_expired",
+    channel: "billing",
+  },
+  StartCheckout: {
+    name: "checkout_started",
+    channel: "billing",
+  },
+  ReachLimit: {
+    name: "limit_reached",
+    channel: "billing",
+  },
+  PreviewImport: {
+    name: "import_previewed",
+    channel: "import",
+  },
+  RunImport: {
+    name: "import_completed",
+    channel: "import",
+  },
+  InstallSlackAgent: {
+    name: "slack_agent_installed",
+    channel: "integration",
+  },
+  EnableSso: {
+    name: "sso_enabled",
+    channel: "workspace",
+  },
+  SubmitFeedback: {
+    name: "feedback_submitted",
+    channel: "feedback",
+  },
   GlobalSpeedChecker: {
     name: "global_speed_checker",
     channel: "checker",
diff --git a/packages/analytics/src/server.ts b/packages/analytics/src/server.ts
index b125203b9..59811929f 100644
--- a/packages/analytics/src/server.ts
+++ b/packages/analytics/src/server.ts
@@ -11,24 +11,37 @@ import type { EventProps } from "./events";
 // Constructing it here also keeps importing this module side-effect free — a
 // top-level `new OpenPanel()` runs the node SDK at import time, which breaks
 // bundling the tRPC context into the Edge runtime.
-function createClient() {
+function createClient(props: IdentifyProps) {
   const client = new OpenPanel({
     clientId: env.NEXT_PUBLIC_OPENPANEL_CLIENT_ID,
     clientSecret: env.OPENPANEL_CLIENT_SECRET,
   });
   client.setGlobalProperties({
     env: process.env.VERCEL_ENV || env.NODE_ENV || "localhost",
-    // app_version
+    source: props.source,
+    plan: props.plan,
   });
   return client;
 }
 
+export type AnalyticsSource =
+  | "dashboard"
+  | "api"
+  | "mcp"
+  | "slack"
+  | "stripe"
+  | "workflows"
+  | "web";
+
 export type IdentifyProps = {
   userId?: string;
   fullName?: string | null;
   email?: string;
   workspaceId?: string;
+  // Upserts the workspace group; without it events still join the group.
+  workspaceName?: string | null;
   plan?: "free" | "starter" | "team" | "scale";
+  source?: AnalyticsSource;
   // headers from the request
   location?: string;
   userAgent?: string;
@@ -39,7 +52,7 @@ export async function setupAnalytics(props: IdentifyProps) {
     return noop();
   }
 
-  const op = createClient();
+  const op = createClient(props);
 
   if (props.location) {
     op.api.addHeader("x-client-ip", props.location);
@@ -56,17 +69,27 @@ export async function setupAnalytics(props: IdentifyProps) {
       email: props.email,
       firstName: firstName,
       lastName: lastName,
-      properties: {
-        workspaceId: props.workspaceId,
-        plan: props.plan,
-      },
     });
   }
 
+  const groupId = props.workspaceId ? `ws_${props.workspaceId}` : undefined;
+  if (groupId && props.workspaceName) {
+    await op.upsertGroup({
+      id: groupId,
+      type: "workspace",
+      name: props.workspaceName,
+      properties: props.plan ? { plan: props.plan } : undefined,
+    });
+  }
+  // Records membership on the profile; events without a profile only carry `groups`.
+  if (groupId && props.userId) {
+    await op.setGroup(groupId);
+  }
+
   return {
     track: (opts: EventProps & TrackProperties) => {
       const { name, ...rest } = opts;
-      return op.track(name, rest);
+      return op.track(name, groupId ? { ...rest, groups: [groupId] } : rest);
     },
   };
 }
diff --git a/packages/api/src/router/feedback.ts b/packages/api/src/router/feedback.ts
index 43b4a870d..c19a51872 100644
--- a/packages/api/src/router/feedback.ts
+++ b/packages/api/src/router/feedback.ts
@@ -1,3 +1,4 @@
+import { Events } from "@openstatus/analytics";
 import {
   feedback,
   feedbackSource,
@@ -10,6 +11,10 @@ import { createTRPCRouter, protectedProcedure } from "../trpc";
 
 export const feedbackRouter = createTRPCRouter({
   submit: protectedProcedure
+    .meta({
+      track: Events.SubmitFeedback,
+      trackProps: ["source", "type", "blocker"],
+    })
     .input(
       z.object({
         message: z.string().trim().min(1, "Message required"),
diff --git a/packages/api/src/router/import.ts b/packages/api/src/router/import.ts
index 07d54445c..f77cab3df 100644
--- a/packages/api/src/router/import.ts
+++ b/packages/api/src/router/import.ts
@@ -1,3 +1,4 @@
+import { Events } from "@openstatus/analytics";
 import {
   PreviewImportInput,
   RunImportInput,
@@ -10,6 +11,7 @@ import { createTRPCRouter, protectedProcedure } from "../trpc";
 
 export const importRouter = createTRPCRouter({
   preview: protectedProcedure
+    .meta({ track: Events.PreviewImport, trackProps: ["provider"] })
     .input(PreviewImportInput)
     .mutation(async ({ ctx, input }) => {
       try {
@@ -20,6 +22,18 @@ export const importRouter = createTRPCRouter({
     }),
 
   run: protectedProcedure
+    .meta({
+      track: Events.RunImport,
+      trackProps: ["provider"],
+      // A summary is returned for failed runs too; only count imports that
+      // actually wrote something.
+      trackResult: ({ data }) => {
+        const status = (data as { status?: string } | undefined)?.status;
+        return status === "completed" || status === "partial"
+          ? { status }
+          : null;
+      },
+    })
     .input(RunImportInput)
     .mutation(async ({ ctx, input }) => {
       try {
diff --git a/packages/api/src/router/invitation.ts b/packages/api/src/router/invitation.ts
index 6932bf777..3aa1101e8 100644
--- a/packages/api/src/router/invitation.ts
+++ b/packages/api/src/router/invitation.ts
@@ -15,7 +15,7 @@ import { createTRPCRouter, protectedProcedure } from "../trpc";
 
 export const invitationRouter = createTRPCRouter({
   create: protectedProcedure
-    .meta({ track: Events.InviteUser, trackProps: ["email"] })
+    .meta({ track: Events.InviteUser })
     .input(CreateInvitationInput)
     .mutation(async ({ ctx, input }) => {
       try {
diff --git a/packages/api/src/router/notification.ts b/packages/api/src/router/notification.ts
index bc2419a37..e967c53de 100644
--- a/packages/api/src/router/notification.ts
+++ b/packages/api/src/router/notification.ts
@@ -138,6 +138,7 @@ export const notificationRouter = createTRPCRouter({
     }),
 
   sendTest: protectedProcedure
+    .meta({ track: Events.TestNotification, trackProps: ["provider"] })
     .input(
       z.object({
         provider: z.enum(notificationProvider),
diff --git a/packages/api/src/router/sso.ts b/packages/api/src/router/sso.ts
index e198707b9..92256f43a 100644
--- a/packages/api/src/router/sso.ts
+++ b/packages/api/src/router/sso.ts
@@ -1,3 +1,4 @@
+import { Events } from "@openstatus/analytics";
 import {
   CreateSsoPortalLinkInput,
   createSsoPortalLink,
@@ -18,13 +19,15 @@ export const ssoRouter = createTRPCRouter({
     }
   }),
 
-  enable: protectedProcedure.mutation(async ({ ctx }) => {
-    try {
-      return await enableSso({ ctx: toServiceCtx(ctx) });
-    } catch (err) {
-      toTRPCError(err);
-    }
-  }),
+  enable: protectedProcedure
+    .meta({ track: Events.EnableSso })
+    .mutation(async ({ ctx }) => {
+      try {
+        return await enableSso({ ctx: toServiceCtx(ctx) });
+      } catch (err) {
+        toTRPCError(err);
+      }
+    }),
 
   disable: protectedProcedure.mutation(async ({ ctx }) => {
     try {
diff --git a/packages/api/src/router/statusPage.ts b/packages/api/src/router/statusPage.ts
index e02809e87..237281e93 100644
--- a/packages/api/src/router/statusPage.ts
+++ b/packages/api/src/router/statusPage.ts
@@ -1323,7 +1323,7 @@ export const statusPageRouter = createTRPCRouter({
     }),
 
   subscribe: publicProcedure
-    .meta({ track: Events.SubscribePage, trackProps: ["slug", "email"] })
+    .meta({ track: Events.SubscribePage, trackProps: ["slug"] })
     .input(
       z.object({
         slug: z.string().toLowerCase(),
@@ -1458,7 +1458,7 @@ export const statusPageRouter = createTRPCRouter({
     }),
 
   validateEmailDomain: publicProcedure
-    .meta({ track: Events.ValidateEmailDomain, trackProps: ["slug", "email"] })
+    .meta({ track: Events.ValidateEmailDomain, trackProps: ["slug"] })
     .input(z.object({ slug: z.string().toLowerCase(), email: z.string() }))
     .query(async (opts) => {
       if (!opts.input.slug) return null;
diff --git a/packages/api/src/router/stripe/index.ts b/packages/api/src/router/stripe/index.ts
index d6d7d4b99..e9c34e430 100644
--- a/packages/api/src/router/stripe/index.ts
+++ b/packages/api/src/router/stripe/index.ts
@@ -110,6 +110,15 @@ async function createPaymentMethodSetupSession(args: {
   });
 }
 
+const checkoutSessionInput = z.object({
+  currency: z.string(),
+  workspaceSlug: z.string(),
+  plan: z.enum(workspacePlans),
+  interval: z.enum(billingIntervals).default("monthly"),
+  successUrl: z.string().optional(),
+  cancelUrl: z.string().optional(),
+});
+
 export const stripeRouter = createTRPCRouter({
   // The workspace only stores the plan, not the interval it is billed on, so
   // the plan table asks Stripe to tell "Pro monthly" apart from "Pro yearly".
@@ -149,16 +158,22 @@ export const stripeRouter = createTRPCRouter({
     }),
 
   getCheckoutSession: protectedProcedure
-    .input(
-      z.object({
-        currency: z.string(),
-        workspaceSlug: z.string(),
-        plan: z.enum(workspacePlans),
-        interval: z.enum(billingIntervals).default("monthly"),
-        successUrl: z.string().optional(),
-        cancelUrl: z.string().optional(),
-      }),
-    )
+    .meta({
+      track: Events.StartCheckout,
+      // Only the final branch opens a Stripe checkout; the setup-session and
+      // in-place plan change paths are not checkouts. Re-parse the raw input so
+      // the defaulted `interval` is tracked too.
+      trackResult: ({ input, data }) => {
+        if ((data as { type?: string } | undefined)?.type !== "checkout") {
+          return null;
+        }
+        const parsed = checkoutSessionInput.safeParse(input);
+        if (!parsed.success) return {};
+        const { plan, interval, currency } = parsed.data;
+        return { plan, interval, currency };
+      },
+    })
+    .input(checkoutSessionInput)
     .mutation(async (opts) => {
       const resolved = await resolveWorkspaceCtx(opts);
       if (!resolved) return;
diff --git a/packages/api/src/router/stripe/utils.test.ts b/packages/api/src/router/stripe/utils.test.ts
index 50378bae3..491036e4e 100644
--- a/packages/api/src/router/stripe/utils.test.ts
+++ b/packages/api/src/router/stripe/utils.test.ts
@@ -9,6 +9,7 @@ import type Stripe from "stripe";
 import {
   FEATURES,
   PLANS,
+  billingProps,
   buildLimitsFromSubscription,
   buildPlanChangeItems,
   getPriceIdForFeature,
@@ -350,3 +351,44 @@ describe("buildPlanChangeItems", () => {
     ).toThrow();
   });
 });
+
+describe("billingProps", () => {
+  const subscription = (
+    interval: "month" | "year",
+    items: { unit_amount: number | null; quantity?: number }[],
+  ) =>
+    ({
+      currency: "usd",
+      items: {
+        data: items.map(({ unit_amount, quantity }) => ({
+          price: { unit_amount, recurring: { interval } },
+          quantity,
+        })),
+      },
+    }) as unknown as Stripe.Subscription;
+
+  test("sums monthly items times quantity, in major units", () => {
+    expect(
+      billingProps(
+        subscription("month", [
+          { unit_amount: 3000 },
+          { unit_amount: 500, quantity: 2 },
+        ]),
+      ),
+    ).toEqual({ interval: "month", currency: "usd", mrr: 40 });
+  });
+
+  test("normalises yearly prices to a monthly amount", () => {
+    expect(
+      billingProps(subscription("year", [{ unit_amount: 36000 }])).mrr,
+    ).toBe(30);
+  });
+
+  test("counts items without a unit amount as zero", () => {
+    expect(
+      billingProps(
+        subscription("month", [{ unit_amount: null }, { unit_amount: 1000 }]),
+      ).mrr,
+    ).toBe(10);
+  });
+});
diff --git a/packages/api/src/router/stripe/utils.ts b/packages/api/src/router/stripe/utils.ts
index 6abffec0c..d161ff261 100644
--- a/packages/api/src/router/stripe/utils.ts
+++ b/packages/api/src/router/stripe/utils.ts
@@ -359,3 +359,18 @@ export const FEATURES = [
     yearly: PriceIds;
   };
 }>;
+
+// List price only: discounts and prorations are not reflected.
+export function billingProps(subscription: Stripe.Subscription) {
+  const items = subscription.items.data;
+  const interval = items[0]?.price.recurring?.interval;
+  const total = items.reduce(
+    (sum, item) => sum + (item.price.unit_amount ?? 0) * (item.quantity ?? 1),
+    0,
+  );
+  return {
+    interval,
+    currency: subscription.currency,
+    mrr: (interval === "year" ? total / 12 : total) / 100,
+  };
+}
diff --git a/packages/api/src/router/stripe/webhook.ts b/packages/api/src/router/stripe/webhook.ts
index 7a3cfc211..7ffe3b095 100644
--- a/packages/api/src/router/stripe/webhook.ts
+++ b/packages/api/src/router/stripe/webhook.ts
@@ -1,6 +1,4 @@
-import { Events, setupAnalytics } from "@openstatus/analytics";
-import { eq } from "@openstatus/db";
-import { user } from "@openstatus/db/src/schema";
+import { type EventProps, Events, setupAnalytics } from "@openstatus/analytics";
 import {
   billingRecipients,
   cancelScheduledEmail,
@@ -39,6 +37,7 @@ import {
   syncedLimits,
   trialEndsAtOf,
 } from "./shared";
+import { billingProps } from "./utils";
 
 const webhookProcedure = publicProcedure.input(
   z.object({
@@ -110,9 +109,43 @@ function toPlanLoss(
   };
 }
 
+type StripeWorkspace = NonNullable<
+  Awaited<ReturnType<typeof getWorkspaceByStripeId>>
+>;
+
+// Never throws: runs after DB writes and emails, so a failure here would make
+// Stripe redeliver the event and resend them.
+async function trackForWorkspaceOwner(args: {
+  db: NonNullable<Db>;
+  ws: StripeWorkspace;
+  event: EventProps;
+  props?: Record<string, unknown>;
+}) {
+  try {
+    const owners = await listWorkspaceOwners({
+      input: { workspaceId: args.ws.id },
+      db: args.db,
+    });
+    // Owners come back unordered: with several, picking one would attribute
+    // billing to an arbitrary profile, so only the workspace group gets it.
+    const owner = owners.length === 1 ? owners[0] : undefined;
+    const analytics = await setupAnalytics({
+      userId: owner ? `usr_${owner.id}` : undefined,
+      email: owner?.email ?? undefined,
+      workspaceId: String(args.ws.id),
+      workspaceName: args.ws.name || args.ws.slug,
+      plan: args.ws.plan ?? undefined,
+      source: "stripe",
+    });
+    await analytics.track({ ...args.props, ...args.event });
+  } catch (err) {
+    console.error(`Failed to track ${args.event.name}:`, err);
+  }
+}
+
 async function sendCancellationEmails(args: {
   db: NonNullable<Db>;
-  ws: NonNullable<Awaited<ReturnType<typeof getWorkspaceByStripeId>>>;
+  ws: StripeWorkspace;
   customerId: string;
   current: Stripe.Subscription;
   plan: string;
@@ -191,6 +224,7 @@ async function attachSetupPaymentMethod(session: Stripe.Checkout.Session) {
   await stripe.subscriptions.update(subscriptionId, {
     default_payment_method: paymentMethod,
   });
+  return subscription;
 }
 
 // Never mount this on an app router: the procedures trust `event`, and only
@@ -318,53 +352,57 @@ export const webhookRouter = createTRPCRouter({
       wasTrialing &&
       current.status === "active"
     ) {
-      const [owner] = await listWorkspaceOwners({
-        input: { workspaceId: ws.id },
+      await trackForWorkspaceOwner({
         db: opts.ctx.db,
+        ws: { ...ws, plan: built.plan },
+        event: Events.ConvertTrial,
+        props: { toPlan: built.plan, ...billingProps(current) },
       });
-      const analytics = await setupAnalytics({
-        userId: owner ? `usr_${owner.id}` : undefined,
-        email: owner?.email ?? undefined,
-        workspaceId: String(ws.id),
-        plan: built.plan,
-      });
-      await analytics.track(Events.ConvertTrial);
     }
 
     const newPlan = built.plan;
     if (newPlan !== oldPlan) {
-      const customer = await stripe.customers.retrieve(customerId);
-      if (!customer.deleted && customer.email) {
-        const userResult = await opts.ctx.db
-          .select()
-          .from(user)
-          .where(eq(user.email, customer.email))
-          .get();
-        if (!userResult) return;
-
-        const planOrder = ["free", "starter", "team", "scale"] as const;
-        const oldIndex = planOrder.indexOf(oldPlan ?? "free");
-        const newIndex = planOrder.indexOf(newPlan ?? "free");
-
-        const event =
+      const planOrder = ["free", "starter", "team", "scale"] as const;
+      const oldIndex = planOrder.indexOf(oldPlan ?? "free");
+      const newIndex = planOrder.indexOf(newPlan ?? "free");
+
+      await trackForWorkspaceOwner({
+        db: opts.ctx.db,
+        ws: { ...ws, plan: newPlan },
+        event:
           newIndex > oldIndex
             ? Events.UpgradeWorkspace
-            : Events.DowngradeWorkspace;
-
-        const analytics = await setupAnalytics({
-          userId: `usr_${userResult.id}`,
-          email: userResult.email || undefined,
-          workspaceId: String(ws.id),
-          plan: newPlan,
-        });
-        await analytics.track(event);
-      }
+            : Events.DowngradeWorkspace,
+        props: { fromPlan: oldPlan, toPlan: newPlan, ...billingProps(current) },
+      });
     }
   }),
   sessionCompleted: webhookProcedure.mutation(async (opts) => {
     const session = opts.input.event.data.object as Stripe.Checkout.Session;
     if (session.mode === "setup") {
-      await attachSetupPaymentMethod(session);
+      const subscription = await attachSetupPaymentMethod(session);
+      if (!subscription) return;
+      const ws = await getWorkspaceByStripeId({
+        input: { stripeId: customerIdOf(subscription) },
+        db: opts.ctx.db,
+      });
+      if (!ws) return;
+      await trackForWorkspaceOwner({
+        db: opts.ctx.db,
+        ws,
+        event: Events.AddTrialPaymentMethod,
+        props: {
+          subscriptionStatus: subscription.status,
+          trialDaysLeft: subscription.trial_end
+            ? Math.max(
+                0,
+                Math.ceil(
+                  (subscription.trial_end * 1000 - Date.now()) / 86_400_000,
+                ),
+              )
+            : undefined,
+        },
+      });
       return;
     }
     if (typeof session.subscription !== "string") {
@@ -433,23 +471,17 @@ export const webhookRouter = createTRPCRouter({
       },
     });
 
-    const customer = await stripe.customers.retrieve(customerId);
-    if (!customer.deleted && customer.email) {
-      const userResult = await opts.ctx.db
-        .select()
-        .from(user)
-        .where(eq(user.email, customer.email))
-        .get();
-      if (!userResult) return;
-
-      const analytics = await setupAnalytics({
-        userId: `usr_${userResult.id}`,
-        email: userResult.email || undefined,
-        workspaceId: String(ws.id),
-        plan: built.plan,
-      });
-      await analytics.track(Events.UpgradeWorkspace);
-    }
+    await trackForWorkspaceOwner({
+      db: opts.ctx.db,
+      ws: { ...ws, plan: built.plan },
+      event: Events.UpgradeWorkspace,
+      props: {
+        fromPlan: ws.plan,
+        toPlan: built.plan,
+        trialing: subscription.status === "trialing",
+        ...billingProps(subscription),
+      },
+    });
   }),
   customerSubscriptionTrialWillEnd: webhookProcedure.mutation(async (opts) => {
     const subscription = opts.input.event.data.object as Stripe.Subscription;
@@ -502,6 +534,13 @@ export const webhookRouter = createTRPCRouter({
         ? toPlanLoss(preview, preview.customDomains, preview.ssoEnabled)
         : undefined,
     });
+
+    await trackForWorkspaceOwner({
+      db: opts.ctx.db,
+      ws,
+      event: Events.NotifyTrialEnding,
+      props: { hasPaymentMethod: withCard },
+    });
   }),
   customerSubscriptionDeleted: webhookProcedure.mutation(async (opts) => {
     const subscription = opts.input.event.data.object as Stripe.Subscription;
@@ -605,23 +644,14 @@ export const webhookRouter = createTRPCRouter({
       }
     }
 
-    const customer = await stripe.customers.retrieve(customerId);
-
-    if (!customer.deleted && customer.email) {
-      const userResult = await opts.ctx.db
-        .select()
-        .from(user)
-        .where(eq(user.email, customer.email))
-        .get();
-      if (!userResult) return;
-
-      const analytics = await setupAnalytics({
-        userId: `usr_${userResult.id}`,
-        email: customer.email || undefined,
-        workspaceId: String(ws.id),
-        plan: "free",
-      });
-      await analytics.track(Events.DowngradeWorkspace);
-    }
+    await trackForWorkspaceOwner({
+      db: opts.ctx.db,
+      ws: { ...ws, plan: "free" },
+      event:
+        reason === "subscription_deleted"
+          ? Events.DowngradeWorkspace
+          : Events.ExpireTrial,
+      props: { fromPlan: ws.plan, toPlan: "free", reason },
+    });
   }),
 });
diff --git a/packages/api/src/service-adapter.ts b/packages/api/src/service-adapter.ts
index 083c65637..b1425dad4 100644
--- a/packages/api/src/service-adapter.ts
+++ b/packages/api/src/service-adapter.ts
@@ -66,6 +66,7 @@ export function toTRPCError(err: unknown): never {
         throw new TRPCError({
           code: "TOO_MANY_REQUESTS",
           message: err.message,
+          cause: err,
         });
       case "PRECONDITION_FAILED":
         throw new TRPCError({
diff --git a/packages/api/src/trpc.ts b/packages/api/src/trpc.ts
index c36e4e81a..26fe80120 100644
--- a/packages/api/src/trpc.ts
+++ b/packages/api/src/trpc.ts
@@ -1,11 +1,13 @@
 import {
   type EventProps,
+  Events,
   type IdentifyProps,
   parseInputToProps,
   setupAnalytics,
 } from "@openstatus/analytics";
 import { db } from "@openstatus/db";
 import type { User, Workspace } from "@openstatus/db/src/schema";
+import { LimitExceededError } from "@openstatus/services";
 import { TRPCError, initTRPC } from "@trpc/server";
 import { type NextRequest, after } from "next/server.js";
 import superjson from "superjson";
@@ -50,6 +52,14 @@ type CreateContextOptions = {
 type Meta = {
   track?: EventProps;
   trackProps?: string[];
+  /**
+   * Props derived from the raw input and the procedure's result, merged over
+   * `trackProps`. Return `null` to skip the event for this call.
+   */
+  trackResult?: (args: {
+    input: unknown;
+    data: unknown;
+  }) => Record<string, unknown> | null;
 };
 
 /**
@@ -250,37 +260,54 @@ const enforceUserIsAuthed = t.middleware(async (opts) => {
     return result;
   }
 
-  // REMINDER: We only track the event if the request was successful
+  const identify: IdentifyProps = {
+    userAgent: ctx.metadata?.userAgent,
+    location: ctx.metadata?.location,
+    source: "dashboard",
+    userId: `usr_${user.id}`,
+    email: user.email || undefined,
+    workspaceId: String(workspace.id),
+    workspaceName: workspace.name || workspace.slug,
+    plan: workspace.plan,
+  };
+
   if (!result.ok) {
+    const cause = result.error.cause;
+    if (cause instanceof LimitExceededError) {
+      after(async () => {
+        const analytics = await setupAnalytics(identify);
+        await analytics.track({
+          ...Events.ReachLimit,
+          limit: cause.limit,
+          max: cause.max,
+          current: cause.current,
+          procedure: opts.path,
+        });
+      });
+    }
     return result;
   }
 
   // REMINDER: We only track the event if the request was successful
   // REMINDER: We are not blocking the request
   after(async () => {
-    const { ctx, meta, getRawInput } = opts;
+    const { meta, getRawInput } = opts;
 
     if (meta?.track) {
-      let identify: IdentifyProps = {
-        userAgent: ctx.metadata?.userAgent,
-        location: ctx.metadata?.location,
-      };
-
-      if (user && workspace) {
-        identify = {
-          ...identify,
-          userId: `usr_${user.id}`,
-          email: user.email || undefined,
-          workspaceId: String(workspace.id),
-          plan: workspace.plan,
-        };
-      }
+      const rawInput = await getRawInput();
+      const resultProps = meta.trackResult
+        ? meta.trackResult({ input: rawInput, data: result.data })
+        : {};
+      if (resultProps === null) return;
 
       const analytics = await setupAnalytics(identify);
-      const rawInput = await getRawInput();
       const additionalProps = parseInputToProps(rawInput, meta.trackProps);
 
-      await analytics.track({ ...meta.track, ...additionalProps });
+      await analytics.track({
+        ...additionalProps,
+        ...resultProps,
+        ...meta.track,
+      });
     }
   });
 
diff --git a/packages/services/src/errors.ts b/packages/services/src/errors.ts
index e50454d8d..d6e574fc5 100644
--- a/packages/services/src/errors.ts
+++ b/packages/services/src/errors.ts
@@ -57,7 +57,7 @@ export class ValidationError extends ServiceError {
 
 export class LimitExceededError extends ServiceError {
   constructor(
-    limit: string,
+    public limit: string,
     public max: number,
     /** Actual usage when the caller counted it — surfaced in client error metadata. */
     public current?: number,