diff --git a/packages/app-store/googlecalendar/lib/CalendarService.ts b/packages/app-store/googlecalendar/lib/CalendarService.ts
index 3366a4c11e38b4..72924189d2609a 100644
--- a/packages/app-store/googlecalendar/lib/CalendarService.ts
+++ b/packages/app-store/googlecalendar/lib/CalendarService.ts
@@ -62,6 +62,7 @@ export default class GoogleCalendarService implements Calendar {
         // `Failed to refresh access token for Google Calendar: userId: ${credential.userId}`
         // );
         this.log.error("Error refreshing google token", err);
+        Sentry.captureException(err);
       }
       return myGoogleAuth;
     };
@@ -339,7 +340,10 @@ export default class GoogleCalendarService implements Calendar {
               },
             },
             (err, apires) => {
-              if (err) return reject(err);
+              if (err) {
+                Sentry.captureException(err);
+                return reject(err);
+              }
               // If there's no calendar we just skip
               if (!apires?.data.calendars) return resolve([]);
               const result = Object.values(apires.data.calendars).reduce((c, i) => {
diff --git a/packages/core/CalendarManager.ts b/packages/core/CalendarManager.ts
index 30d4dba73242de..ce522ed9dcda62 100644
--- a/packages/core/CalendarManager.ts
+++ b/packages/core/CalendarManager.ts
@@ -1,4 +1,5 @@
 import { SelectedCalendar } from "@prisma/client";
+import * as Sentry from "@sentry/nextjs";
 import { createHash } from "crypto";
 import _ from "lodash";
 
@@ -186,6 +187,12 @@ export const getBusyCalendarTimes = async (
       calendars: selectedCalendars,
       credentials: withCredentials,
     });
+    Sentry.captureException(error, {
+      extra: {
+        calendars: selectedCalendars,
+        credentials: withCredentials,
+      },
+    });
   }
   return results.reduce((acc, availability) => acc.concat(availability), []);
 };
diff --git a/packages/features/bookings/lib/handleCancelBooking.ts b/packages/features/bookings/lib/handleCancelBooking.ts
index 403e94339c89a0..81998f09d73f8a 100644
--- a/packages/features/bookings/lib/handleCancelBooking.ts
+++ b/packages/features/bookings/lib/handleCancelBooking.ts
@@ -6,6 +6,7 @@ import {
   WorkflowMethods,
   WorkflowReminder,
 } from "@prisma/client";
+import * as Sentry from "@sentry/nextjs";
 import { NextApiRequest } from "next";
 
 import { getCalendar } from "@calcom/app-store/_utils/getCalendar";
@@ -182,6 +183,7 @@ async function handler(req: NextApiRequest & { userId?: number }) {
       smsReminderNumber: bookingToDelete.smsReminderNumber || undefined,
     }).catch((e) => {
       console.error(`Error executing webhook for event: ${eventTrigger}, URL: ${webhook.subscriberUrl}`, e);
+      Sentry.captureException(e);
     })
   );
   await Promise.all(promises);
diff --git a/packages/features/bookings/lib/handleNewBooking.ts b/packages/features/bookings/lib/handleNewBooking.ts
index a9ad9acd9ad35a..f71e732842869c 100644
--- a/packages/features/bookings/lib/handleNewBooking.ts
+++ b/packages/features/bookings/lib/handleNewBooking.ts
@@ -6,6 +6,7 @@ import {
   SchedulingType,
   WebhookTriggerEvents,
 } from "@prisma/client";
+import * as Sentry from "@sentry/nextjs";
 import async from "async";
 import { isValidPhoneNumber } from "libphonenumber-js";
 import { cloneDeep } from "lodash";
@@ -243,10 +244,11 @@ async function ensureAvailableUsers(
       } else {
         isAvailableToBeBooked = isAvailable(bufferedBusyTimes, input.dateFrom, eventType.length);
       }
-    } catch {
+    } catch (e) {
       log.debug({
         message: "Unable set isAvailableToBeBooked. Using true. ",
       });
+      Sentry.captureException(e);
     }
 
     if (isAvailableToBeBooked) {
@@ -311,6 +313,7 @@ async function handler(req: NextApiRequest & { userId?: number | undefined }) {
     log.debug({
       message: "Unable set timeOutOfBounds. Using false. ",
     });
+    Sentry.captureException(error);
   }
 
   if (timeOutOfBounds) {
@@ -772,6 +775,9 @@ async function handler(req: NextApiRequest & { userId?: number | undefined }) {
   } catch (_err) {
     const err = getErrorFromUnknown(_err);
     log.error(`Booking ${eventTypeId} failed`, "Error when saving booking to db", err.message);
+
+    Sentry.captureException(err);
+
     if (err.code === "P2002") {
       throw new HttpError({ statusCode: 409, message: "booking.conflict" });
     }
@@ -1007,6 +1013,7 @@ async function handler(req: NextApiRequest & { userId?: number | undefined }) {
       });
     } catch (error) {
       log.error("Error while running scheduledJobs for booking", error);
+      Sentry.captureException(error);
     }
 
     try {
@@ -1041,11 +1048,13 @@ async function handler(req: NextApiRequest & { userId?: number | undefined }) {
           smsReminderNumber: booking?.smsReminderNumber || undefined,
         }).catch((e) => {
           console.error(`Error executing webhook for event: ${eventTrigger}, URL: ${sub.subscriberUrl}`, e);
+          Sentry.captureException(e);
         })
       );
       await Promise.all(promises);
     } catch (error) {
       log.error("Error while sending webhook", error);
+      Sentry.captureException(error);
     }
   }
 
@@ -1067,6 +1076,7 @@ async function handler(req: NextApiRequest & { userId?: number | undefined }) {
     }
   } catch (error) {
     log.error("Error while updating hashed link", error);
+    Sentry.captureException(error);
   }
 
   if (!booking) throw new HttpError({ statusCode: 400, message: "Booking failed" });
@@ -1087,6 +1097,7 @@ async function handler(req: NextApiRequest & { userId?: number | undefined }) {
     });
   } catch (error) {
     log.error("Error while creating booking references", error);
+    Sentry.captureException(error);
   }
 
   try {
@@ -1100,6 +1111,7 @@ async function handler(req: NextApiRequest & { userId?: number | undefined }) {
     );
   } catch (error) {
     log.error("Error while scheduling workflow reminders", error);
+    Sentry.captureException(error);
   }
 
   // booking successful