diff --git a/apps/web/app/(all)/[workspaceSlug]/(settings)/settings/(workspace)/project-states/page.tsx b/apps/web/app/(all)/[workspaceSlug]/(settings)/settings/(workspace)/project-states/page.tsx
index 42cf79cf33..d624c3d624 100644
--- a/apps/web/app/(all)/[workspaceSlug]/(settings)/settings/(workspace)/project-states/page.tsx
+++ b/apps/web/app/(all)/[workspaceSlug]/(settings)/settings/(workspace)/project-states/page.tsx
@@ -4,6 +4,7 @@ import React from "react";
 import { observer } from "mobx-react";
 import { useParams } from "next/navigation";
 // plane imports
+import { PROJECT_GROUPING_TRACKER_EVENTS } from "@plane/constants";
 import { useTranslation } from "@plane/i18n";
 import { EUserWorkspaceRoles } from "@plane/types";
 import { ToggleSwitch } from "@plane/ui";
@@ -12,6 +13,7 @@ import { NotAuthorizedView } from "@/components/auth-screens";
 import { PageHead } from "@/components/core";
 // store hooks
 import { SettingsContentWrapper, SettingsHeading } from "@/components/settings";
+import { captureError, captureSuccess } from "@/helpers/event-tracker.helper";
 import { useUserPermissions, useWorkspace } from "@/hooks/store";
 // plane web components
 import { WithFeatureFlagHOC } from "@/plane-web/components/feature-flags";
@@ -44,13 +46,24 @@ const WorklogsPage = observer(() => {
   if (!isAdmin) return <NotAuthorizedView section="settings" className="h-auto" />;
 
   const toggleProjectGroupingFeature = async () => {
+    const willEnableProjectGrouping = !isProjectGroupingEnabled;
     try {
       const payload = {
-        [EWorkspaceFeatures.IS_PROJECT_GROUPING_ENABLED]: !isProjectGroupingEnabled,
+        [EWorkspaceFeatures.IS_PROJECT_GROUPING_ENABLED]: willEnableProjectGrouping,
       };
       await updateWorkspaceFeature(workspaceSlug.toString(), payload);
+      captureSuccess({
+        eventName: willEnableProjectGrouping
+          ? PROJECT_GROUPING_TRACKER_EVENTS.ENABLE
+          : PROJECT_GROUPING_TRACKER_EVENTS.DISABLE,
+      });
     } catch (error) {
       console.error(error);
+      captureError({
+        eventName: willEnableProjectGrouping
+          ? PROJECT_GROUPING_TRACKER_EVENTS.DISABLE
+          : PROJECT_GROUPING_TRACKER_EVENTS.ENABLE,
+      });
     }
   };
 
diff --git a/apps/web/ee/components/license/modal/trial-button.tsx b/apps/web/ee/components/license/modal/trial-button.tsx
index 1a71c2f3c2..6b61d45a19 100644
--- a/apps/web/ee/components/license/modal/trial-button.tsx
+++ b/apps/web/ee/components/license/modal/trial-button.tsx
@@ -4,19 +4,23 @@ import { useState } from "react";
 import { useParams } from "next/navigation";
 // plane imports
 import { Loader } from "lucide-react";
+import { LICENSE_TRACKER_ELEMENTS, LICENSE_TRACKER_EVENTS } from "@plane/constants";
+import { EProductSubscriptionEnum } from "@plane/types";
 import { setToast, TOAST_TYPE } from "@plane/ui";
 import { cn } from "@plane/utils";
 // plane web imports
+import { captureError, captureSuccess } from "@/helpers/event-tracker.helper";
 import { useWorkspaceSubscription } from "@/plane-web/hooks/store";
 
 export type TTrialButtonProps = {
-  productId: string | undefined;
-  priceId: string | undefined;
   handleClose: () => void;
+  priceId: string | undefined;
+  productId: string | undefined;
+  variant: EProductSubscriptionEnum;
 };
 
 export const TrialButton: React.FC<TTrialButtonProps> = (props: TTrialButtonProps) => {
-  const { productId, priceId, handleClose } = props;
+  const { handleClose, productId, priceId, variant } = props;
   // router
   const { workspaceSlug } = useParams();
   // states
@@ -39,6 +43,12 @@ export const TrialButton: React.FC<TTrialButtonProps> = (props: TTrialButtonProp
       await freeTrialSubscription(workspaceSlug.toString(), { product_id: productId, price_id: priceId });
       handleClose();
       handleSuccessModalToggle(true);
+      captureSuccess({
+        eventName: LICENSE_TRACKER_EVENTS.trial_started,
+        payload: {
+          plan: variant,
+        },
+      });
     } catch (error) {
       const currentError = error as unknown as { error: string; detail: string };
       console.error("Error in freeTrialSubscription", error);
@@ -47,6 +57,12 @@ export const TrialButton: React.FC<TTrialButtonProps> = (props: TTrialButtonProp
         title: "Error!",
         message: currentError?.detail ?? currentError?.error ?? "Something went wrong. Please try again.",
       });
+      captureError({
+        eventName: LICENSE_TRACKER_EVENTS.trial_started,
+        payload: {
+          plan: variant,
+        },
+      });
     } finally {
       setTrialLoader(false);
     }
@@ -54,6 +70,7 @@ export const TrialButton: React.FC<TTrialButtonProps> = (props: TTrialButtonProp
 
   return (
     <button
+      data-element={LICENSE_TRACKER_ELEMENTS.MODAL_TRIAL_BUTTON}
       disabled={trialLoader}
       className="text-center text-sm text-custom-text-300 hover:text-custom-text-100 font-medium transition-all flex justify-center items-center gap-1.5 -ml-5"
       onClick={() => handleTrial(productId, priceId)}
diff --git a/apps/web/ee/components/license/modal/upgrade-modal.tsx b/apps/web/ee/components/license/modal/upgrade-modal.tsx
index fa7c056de5..a2f56837cf 100644
--- a/apps/web/ee/components/license/modal/upgrade-modal.tsx
+++ b/apps/web/ee/components/license/modal/upgrade-modal.tsx
@@ -8,6 +8,8 @@ import useSWR from "swr";
 import {
   BUSINESS_PLAN_FEATURES,
   ENTERPRISE_PLAN_FEATURES,
+  LICENSE_TRACKER_ELEMENTS,
+  LICENSE_TRACKER_EVENTS,
   PRO_PLAN_FEATURES,
   SUBSCRIPTION_WEBPAGE_URLS,
   SUBSCRIPTION_WITH_TRIAL,
@@ -19,6 +21,7 @@ import { cn, getSubscriptionName } from "@plane/utils";
 import { FreePlanCard, PlanUpgradeCard } from "@/components/license";
 import { TCheckoutParams } from "@/components/license/modal/card/checkout-button";
 // plane web imports
+import { captureClick, captureError, captureSuccess } from "@/helpers/event-tracker.helper";
 import { useSelfHostedSubscription, useWorkspaceSubscription } from "@/plane-web/hooks/store";
 import { PaymentService } from "@/plane-web/services/payment.service";
 // local imports
@@ -71,12 +74,18 @@ export const PaidPlanUpgradeModal: FC<PaidPlanUpgradeModalProps> = observer((pro
   );
 
   const handleStripeCheckout = ({ planVariant, productId, priceId }: TCheckoutParams) => {
+    captureClick({
+      elementName: LICENSE_TRACKER_ELEMENTS.MODAL_UPGRADE_BUTTON,
+    });
     if (!productId || !priceId) {
       setToast({
         type: TOAST_TYPE.ERROR,
         title: "Error!",
         message: "Unable to get the product id or price id. Please try again.",
       });
+      captureError({
+        eventName: LICENSE_TRACKER_EVENTS.upgrade_product_or_price_not_found,
+      });
       return;
     }
     setUpgradeLoaderType(planVariant);
@@ -88,6 +97,9 @@ export const PaidPlanUpgradeModal: FC<PaidPlanUpgradeModalProps> = observer((pro
       .then((response) => {
         if (response.url) {
           window.open(response.url, "_blank");
+          captureSuccess({
+            eventName: LICENSE_TRACKER_EVENTS.upgrade_url_received,
+          });
         }
       })
       .catch((error) => {
@@ -96,6 +108,9 @@ export const PaidPlanUpgradeModal: FC<PaidPlanUpgradeModalProps> = observer((pro
           title: "Error!",
           message: error?.error ?? "Failed to generate payment link. Please try again.",
         });
+        captureError({
+          eventName: LICENSE_TRACKER_EVENTS.upgrade_url_received,
+        });
       })
       .finally(() => {
         setUpgradeLoaderType(undefined);
@@ -108,7 +123,7 @@ export const PaidPlanUpgradeModal: FC<PaidPlanUpgradeModalProps> = observer((pro
     priceId: string | undefined
   ) => {
     if (SUBSCRIPTION_WITH_TRIAL.includes(variant)) {
-      return <TrialButton productId={productId} priceId={priceId} handleClose={handleClose} />;
+      return <TrialButton handleClose={handleClose} productId={productId} priceId={priceId} variant={variant} />;
     }
     return null;
   };
diff --git a/apps/web/ee/components/workspace/billing/comparison/subscription-button.tsx b/apps/web/ee/components/workspace/billing/comparison/subscription-button.tsx
index c024b8e03b..0cf9f7d828 100644
--- a/apps/web/ee/components/workspace/billing/comparison/subscription-button.tsx
+++ b/apps/web/ee/components/workspace/billing/comparison/subscription-button.tsx
@@ -1,7 +1,7 @@
 import { FC } from "react";
 import { observer } from "mobx-react";
 // plane imports
-import { EProductSubscriptionTier } from "@plane/constants";
+import { EProductSubscriptionTier, LICENSE_TRACKER_ELEMENTS } from "@plane/constants";
 import { useTranslation } from "@plane/i18n";
 import { EProductSubscriptionEnum, IPaymentProduct } from "@plane/types";
 import { Button, getButtonStyling, getUpgradeButtonStyle, Loader } from "@plane/ui";
@@ -73,6 +73,7 @@ export const SubscriptionButton: FC<TSubscriptionButtonProps> = observer((props)
 
     return (
       <button
+        data-ph-element={LICENSE_TRACKER_ELEMENTS.BILLING_PAGE_COMPARISON_SECTION_UPGRADE_BUTTON}
         onClick={() => handleSubscriptionUpgrade(subscriptionType)}
         className={cn(upgradeButtonStyle, COMMON_BUTTON_STYLE)}
         disabled={!!upgradeLoader}
diff --git a/apps/web/ee/components/workspace/billing/comparison/trial-detail.tsx b/apps/web/ee/components/workspace/billing/comparison/trial-detail.tsx
index 867b5a40a3..ca2084053e 100644
--- a/apps/web/ee/components/workspace/billing/comparison/trial-detail.tsx
+++ b/apps/web/ee/components/workspace/billing/comparison/trial-detail.tsx
@@ -1,6 +1,7 @@
 import { FC } from "react";
 import { observer } from "mobx-react";
 import { LoaderIcon } from "lucide-react";
+import { LICENSE_TRACKER_ELEMENTS } from "@plane/constants";
 import { EProductSubscriptionEnum } from "@plane/types";
 // plane imports
 import { Button } from "@plane/ui";
@@ -35,6 +36,7 @@ export const TrialDetails: FC<TTrialDetailsProps> = observer((props) => {
   if (isTrialAllowed) {
     return (
       <Button
+        data-ph-element={LICENSE_TRACKER_ELEMENTS.BILLING_PAGE_TRIAL_BUTTON}
         variant="link-neutral"
         size="sm"
         onClick={() => handleTrial(subscriptionType)}
diff --git a/apps/web/ee/components/workspace/billing/root.tsx b/apps/web/ee/components/workspace/billing/root.tsx
index 0e2b081f4b..1810fad76d 100644
--- a/apps/web/ee/components/workspace/billing/root.tsx
+++ b/apps/web/ee/components/workspace/billing/root.tsx
@@ -3,7 +3,12 @@ import { observer } from "mobx-react";
 import { useParams } from "next/navigation";
 import useSWR from "swr";
 // plane imports
-import { DEFAULT_PRODUCT_BILLING_FREQUENCY, SUBSCRIPTION_WITH_BILLING_FREQUENCY } from "@plane/constants";
+import {
+  DEFAULT_PRODUCT_BILLING_FREQUENCY,
+  LICENSE_TRACKER_ELEMENTS,
+  LICENSE_TRACKER_EVENTS,
+  SUBSCRIPTION_WITH_BILLING_FREQUENCY,
+} from "@plane/constants";
 import { useTranslation } from "@plane/i18n";
 import {
   EProductSubscriptionEnum,
@@ -18,6 +23,7 @@ import { cn, getSubscriptionProduct, getSubscriptionProductPrice } from "@plane/
 // helpers
 import { SettingsHeading } from "@/components/settings";
 // plane web imports
+import { captureClick, captureError, captureSuccess } from "@/helpers/event-tracker.helper";
 import {
   CloudFreePlanCard,
   OnePlanCard,
@@ -92,6 +98,12 @@ export const BillingRoot = observer(() => {
         price_id: selectedPriceId,
       });
       handleSuccessModalToggle(true);
+      captureSuccess({
+        eventName: LICENSE_TRACKER_EVENTS.trial_started,
+        payload: {
+          plan: selectedSubscriptionType,
+        },
+      });
     } catch (error) {
       const currentError = error as unknown as { error: string; detail: string };
       console.error("Error in freeTrialSubscription", error);
@@ -100,6 +112,12 @@ export const BillingRoot = observer(() => {
         title: "Error!",
         message: currentError?.detail ?? currentError?.error ?? "Something went wrong. Please try again.",
       });
+      captureError({
+        eventName: LICENSE_TRACKER_EVENTS.trial_started,
+        payload: {
+          plan: selectedSubscriptionType,
+        },
+      });
     } finally {
       setTrialLoader(null);
     }
@@ -126,6 +144,9 @@ export const BillingRoot = observer(() => {
     }
     if (!selectedProductId || !selectedPriceId) {
       setToast({ type: TOAST_TYPE.ERROR, title: "Error!", message: "Missing product or price ID" });
+      captureError({
+        eventName: LICENSE_TRACKER_EVENTS.upgrade_product_or_price_not_found,
+      });
       return;
     }
     setUpgradeLoader(selectedSubscriptionType);
@@ -136,6 +157,9 @@ export const BillingRoot = observer(() => {
       })
       .then((response) => {
         if (response.url) window.open(response.url, isSelfManaged ? "_blank" : "_self");
+        captureSuccess({
+          eventName: LICENSE_TRACKER_EVENTS.upgrade_url_received,
+        });
       })
       .catch((error) => {
         setToast({
@@ -143,6 +167,9 @@ export const BillingRoot = observer(() => {
           title: "Error!",
           message: error?.error ?? "Failed to generate payment link",
         });
+        captureError({
+          eventName: LICENSE_TRACKER_EVENTS.upgrade_url_received,
+        });
       })
       .finally(() => setUpgradeLoader(null));
   };
@@ -191,6 +218,9 @@ export const BillingRoot = observer(() => {
    */
   const handleSelectedPlanUpgrade = (selectedSubscriptionType: EProductSubscriptionEnum): Promise<void> => {
     const { selectedProduct, selectedPrice } = getSelectedProductAndPrice(selectedSubscriptionType);
+    captureClick({
+      elementName: LICENSE_TRACKER_ELEMENTS.BILLING_PAGE_PLAN_CARD_UPGRADE_BUTTON,
+    });
     return handleUpgradeSubscription({
       selectedSubscriptionType,
       selectedProductId: selectedProduct?.id,
diff --git a/packages/constants/src/event-tracker/extended.ts b/packages/constants/src/event-tracker/extended.ts
index 14fe4eadd0..ea92e1c2d1 100644
--- a/packages/constants/src/event-tracker/extended.ts
+++ b/packages/constants/src/event-tracker/extended.ts
@@ -12,6 +12,22 @@ export const EPIC_TRACKER_ELEMENTS = {
 export const LICENSE_TRACKER_EVENTS = {
   purchase_modal_opened: "purchase_modal_opened",
   success_modal_opened: "success_modal_opened",
+  trial_started: "trial_started",
+  upgrade_url_received: "upgrade_url_received",
+  upgrade_product_or_price_not_found: "upgrade_product_or_price_not_found",
+};
+
+export const LICENSE_TRACKER_ELEMENTS = {
+  MODAL_TRIAL_BUTTON: "modal_trial_button",
+  BILLING_PAGE_TRIAL_BUTTON: "billing_page_trial_button",
+  MODAL_UPGRADE_BUTTON: "modal_upgrade_button",
+  BILLING_PAGE_COMPARISON_SECTION_UPGRADE_BUTTON: "billing_page_comparison_section_upgrade_button",
+  BILLING_PAGE_PLAN_CARD_UPGRADE_BUTTON: "billing_page_plan_card_upgrade_button",
+};
+
+export const PROJECT_GROUPING_TRACKER_EVENTS = {
+  ENABLE: "project_grouping_enabled",
+  DISABLE: "project_grouping_disabled",
 };
 
 export const PROJECT_OVERVIEW_TRACKER_EVENTS = {