diff --git a/src/Admin/Jobs/JobsHostedService.cs b/src/Admin/Jobs/JobsHostedService.cs
index 72bf1d395..06842eaca 100644
--- a/src/Admin/Jobs/JobsHostedService.cs
+++ b/src/Admin/Jobs/JobsHostedService.cs
@@ -31,22 +31,27 @@ namespace Bit.Admin.Jobs
             }
 
             var everyTopOfTheHourTrigger = TriggerBuilder.Create()
+                .WithIdentity("EveryTopOfTheHourTrigger")
                 .StartNow()
                 .WithCronSchedule("0 0 * * * ?")
                 .Build();
             var everyFiveMinutesTrigger = TriggerBuilder.Create()
+                .WithIdentity("EveryFiveMinutesTrigger")
                 .StartNow()
                 .WithCronSchedule("0 */5 * * * ?")
                 .Build();
             var everyFridayAt10pmTrigger = TriggerBuilder.Create()
+                .WithIdentity("EveryFridayAt10pmTrigger")
                 .StartNow()
                 .WithCronSchedule("0 0 22 ? * FRI", x => x.InTimeZone(timeZone))
                 .Build();
             var everySaturdayAtMidnightTrigger = TriggerBuilder.Create()
+                .WithIdentity("EverySaturdayAtMidnightTrigger")
                 .StartNow()
                 .WithCronSchedule("0 0 0 ? * SAT", x => x.InTimeZone(timeZone))
                 .Build();
             var everySundayAtMidnightTrigger = TriggerBuilder.Create()
+                .WithIdentity("EverySundayAtMidnightTrigger")
                 .StartNow()
                 .WithCronSchedule("0 0 0 ? * SUN", x => x.InTimeZone(timeZone))
                 .Build();
diff --git a/src/Api/Jobs/JobsHostedService.cs b/src/Api/Jobs/JobsHostedService.cs
index 06d1d4dad..2b71f6c0a 100644
--- a/src/Api/Jobs/JobsHostedService.cs
+++ b/src/Api/Jobs/JobsHostedService.cs
@@ -22,22 +22,27 @@ namespace Bit.Api.Jobs
         public override async Task StartAsync(CancellationToken cancellationToken)
         {
             var everyTopOfTheHourTrigger = TriggerBuilder.Create()
+                .WithIdentity("EveryTopOfTheHourTrigger")
                 .StartNow()
                 .WithCronSchedule("0 0 * * * ?")
                 .Build();
             var emergencyAccessNotificationTrigger = TriggerBuilder.Create()
+                .WithIdentity("EmergencyAccessNotificationTrigger")
                 .StartNow()
                 .WithCronSchedule("0 0 * * * ?")
                 .Build();
             var emergencyAccessTimeoutTrigger  = TriggerBuilder.Create()
+                .WithIdentity("EmergencyAccessTimeoutTrigger")
                 .StartNow()
                 .WithCronSchedule("0 0 * * * ?")
                 .Build();
             var everyTopOfTheSixthHourTrigger = TriggerBuilder.Create()
+                .WithIdentity("EveryTopOfTheSixthHourTrigger")
                 .StartNow()
                 .WithCronSchedule("0 0 */6 * * ?")
                 .Build();
             var everyTwelfthHourAndThirtyMinutesTrigger = TriggerBuilder.Create()
+                .WithIdentity("EveryTwelfthHourAndThirtyMinutesTrigger")
                 .StartNow()
                 .WithCronSchedule("0 30 */12 * * ?")
                 .Build();
diff --git a/src/Billing/Jobs/JobsHostedService.cs b/src/Billing/Jobs/JobsHostedService.cs
index 9954a0dd0..01cbadac7 100644
--- a/src/Billing/Jobs/JobsHostedService.cs
+++ b/src/Billing/Jobs/JobsHostedService.cs
@@ -31,6 +31,7 @@ namespace Bit.Billing.Jobs
             }
 
             var everyDayAtNinePmTrigger = TriggerBuilder.Create()
+                .WithIdentity("EveryDayAtNinePmTrigger")
                 .StartNow()
                 .WithCronSchedule("0 0 21 * * ?", x => x.InTimeZone(timeZone))
                 .Build();
diff --git a/src/Core/Jobs/BaseJobsHostedService.cs b/src/Core/Jobs/BaseJobsHostedService.cs
index 64c4233ef..72758091a 100644
--- a/src/Core/Jobs/BaseJobsHostedService.cs
+++ b/src/Core/Jobs/BaseJobsHostedService.cs
@@ -1,6 +1,7 @@
 using System;
 using System.Collections.Generic;
 using System.Collections.Specialized;
+using System.Linq;
 using System.Threading;
 using System.Threading.Tasks;
 using Microsoft.Extensions.Hosting;
@@ -65,12 +66,62 @@ namespace Bit.Core.Jobs
             await _scheduler.Start(cancellationToken);
             if (Jobs != null)
             {
-                foreach (var job in Jobs)
+                foreach (var (job, trigger) in Jobs)
                 {
-                    var builtJob = JobBuilder.Create(job.Item1).Build();
-                    await _scheduler.ScheduleJob(builtJob, job.Item2);
+                    var dupeT = await _scheduler.GetTrigger(trigger.Key);
+                    if (dupeT != null)
+                    {
+                        await _scheduler.RescheduleJob(trigger.Key, trigger);
+                    }
+
+                    var jobDetail = JobBuilder.Create(job)
+                        .WithIdentity(job.FullName)
+                        .Build();
+
+                    var dupeJ = await _scheduler.GetJobDetail(jobDetail.Key);
+                    if (dupeJ != null)
+                    {
+                        await _scheduler.DeleteJob(jobDetail.Key);
+                    }
+
+                    await _scheduler.ScheduleJob(jobDetail, trigger);
                 }
             }
+
+            // Delete old Jobs and Triggers
+            var existingJobKeys = await _scheduler.GetJobKeys(GroupMatcher<JobKey>.AnyGroup());
+            var jobKeys = Jobs.Select(j =>
+            {
+                var job = j.Item1;
+                return JobBuilder.Create(job)
+                    .WithIdentity(job.FullName)
+                    .Build().Key;
+            });
+
+            foreach (var key in existingJobKeys)
+            {
+                if (jobKeys.Contains(key))
+                {
+                    continue;
+                }
+
+                _logger.LogInformation($"Deleting old job with key {key}");
+                await _scheduler.DeleteJob(key);
+            }
+
+            var existingTriggerKeys = await _scheduler.GetTriggerKeys(GroupMatcher<TriggerKey>.AnyGroup());
+            var triggerKeys = Jobs.Select(j => j.Item2.Key);
+
+            foreach (var key in existingTriggerKeys)
+            {
+                if (triggerKeys.Contains(key))
+                {
+                    continue;
+                }
+
+                _logger.LogInformation($"Unscheduling old trigger with key {key}");
+                await _scheduler.UnscheduleJob(key);
+            }
         }
 
         public virtual async Task StopAsync(CancellationToken cancellationToken)
diff --git a/src/Notifications/Jobs/JobsHostedService.cs b/src/Notifications/Jobs/JobsHostedService.cs
index e59b0939a..3d78083c6 100644
--- a/src/Notifications/Jobs/JobsHostedService.cs
+++ b/src/Notifications/Jobs/JobsHostedService.cs
@@ -22,6 +22,7 @@ namespace Bit.Notifications.Jobs
         public override async Task StartAsync(CancellationToken cancellationToken)
         {
             var everyFiveMinutesTrigger = TriggerBuilder.Create()
+                .WithIdentity("EveryFiveMinutesTrigger")
                 .StartNow()
                 .WithCronSchedule("0 */30 * * * ?")
                 .Build();