diff --git a/src/backend/scrobblers/AbstractScrobbleClient.ts b/src/backend/scrobblers/AbstractScrobbleClient.ts
index 276d2aba..a8bab9f6 100644
--- a/src/backend/scrobblers/AbstractScrobbleClient.ts
+++ b/src/backend/scrobblers/AbstractScrobbleClient.ts
@@ -287,7 +287,7 @@ export default abstract class AbstractScrobbleClient extends AbstractComponent i
                     'Dead',
                     (): Promise<any> => {
                         if(this.isReady()) {
-                            return this.processDeadLetterQueue().then(() => null).catch((e) => {
+                            return this.processDeadLetterQueue(undefined, 'Reprocessing bulk dead Plays by system').then(() => null).catch((e) => {
                                 this.warnings = e;
                                 this.logger.error(e);
                             })
diff --git a/src/backend/server/api.ts b/src/backend/server/api.ts
index b5693cf3..3bd1502c 100644
--- a/src/backend/server/api.ts
+++ b/src/backend/server/api.ts
@@ -767,7 +767,7 @@ export const setupApi = (args: ApiArgs, opts: ApiOptions = {}) => {
 
         res.status(200).send('OK');
 
-        await ((client as AbstractScrobbleClient).processDeadLetterQueue(1000));
+        await ((client as AbstractScrobbleClient).processDeadLetterQueue(1000, 'Reprocessing bulk dead Plays initiated by user'));
     });
 
     router.put('/api/dead/:id', {middleware: [clientMiddleFunc(true)], hidden: true}, async (req, res, next) => {
diff --git a/src/backend/sources/AbstractSource.ts b/src/backend/sources/AbstractSource.ts
index 7367eced..874094b2 100644
--- a/src/backend/sources/AbstractSource.ts
+++ b/src/backend/sources/AbstractSource.ts
@@ -210,7 +210,7 @@ export default abstract class AbstractSource extends AbstractComponent implement
                     'Dead',
                     (): Promise<any> => {
                         if(this.isReady()) {
-                            return this.processDeadLetterQueue().then(() => null).catch((e) => {
+                            return this.processDeadLetterQueue(undefined, 'Reprocessing bulk dead Plays by system').then(() => null).catch((e) => {
                                 this.warnings = e;
                                 this.logger.error(e);
                             })
diff --git a/src/client/components/ActivityTimeline.tsx b/src/client/components/ActivityTimeline.tsx
index f1edba7a..907e9bd5 100644
--- a/src/client/components/ActivityTimeline.tsx
+++ b/src/client/components/ActivityTimeline.tsx
@@ -1,5 +1,6 @@
 import type { Collapsible } from '@chakra-ui/react';
-import { Card, Text, Icon, SkeletonCircle, SkeletonText, Span, Tabs, Timeline} from '@chakra-ui/react';
+import { Card, Text, Icon, SkeletonCircle, SkeletonText, Span, Tabs, Timeline, Tag, HStack, Stack, Separator} from '@chakra-ui/react';
+import { HiCheck } from "react-icons/hi"
 import dayjs from "dayjs";
 import React from "react";
 import { BiWrench } from "react-icons/bi";
@@ -15,7 +16,7 @@ import { activityTransformHasIssue, timelineIconProps, TimelineItemSummaryText }
 import { ChakraCodeBlockShort } from "./CodeBlock";
 import { ErrorAlert } from "./ErrorAlert";
 import { MSErrorBoundary } from "./ErrorBoundary";
-import { CheckIcon, ExclamationTriangleIcon, TimelineIndicatorIconQueued } from "./icons/ChakraIcons";
+import { CheckIcon, ExclamationTriangleIcon, TimelineIndicatorIconQueued, XIcon } from "./icons/ChakraIcons";
 import { MSCollapsible } from "./MSCollapsible";
 import { PlayData } from "./PlayData";
 import { ScrobbleActionResult } from "./ScrobbleActionResult";
@@ -274,6 +275,20 @@ const ScrobbleResponseItem = (props: Pick<ActivityTimelineProps, 'collapsibleOpe
     )
 }
 
+const RetryChip = (props: { count: number }) => (<Tag.Root>
+    <Tag.Label>Attempt: {props.count}</Tag.Label>
+</Tag.Root>)
+
+const BoolChip = (props: { text: string, check: boolean }) => (<Tag.Root>
+    <Tag.Label>{props.text}</Tag.Label>
+    <Tag.EndElement>
+        {props.check ? <HiCheck /> : <XIcon />}
+    </Tag.EndElement>
+</Tag.Root>)
+const DupeChip = (props: { check: boolean }) => <BoolChip {...props} text="Duplicate Check" />;
+const TransformChip = (props: { check: boolean }) => <BoolChip {...props} text="Transform" />
+const CacheChip = (props: { check: boolean }) => <BoolChip {...props} text="Use Cache" />
+
 const QueueTimelineItem = (props: {queueState: PlayEventQueueStateChange<string>, collapsibleOpen: boolean}) => {
     const {
         queueState: {
@@ -281,7 +296,13 @@ const QueueTimelineItem = (props: {queueState: PlayEventQueueStateChange<string>
                 queueStatus,
                 queueName,
                 error,
-                retries
+                retries,
+                context: {
+                    dupeCheck,
+                    transform,
+                    useCache,
+                    reason
+                } = {}
             },
             createdAt,
         } = {},
@@ -292,6 +313,28 @@ const QueueTimelineItem = (props: {queueState: PlayEventQueueStateChange<string>
     text: React.JSX.Element,
     title: React.JSX.Element;
 
+    const contextHints: React.JSX.Element[] = [];
+    const tags: React.JSX.Element[] = [];
+
+    if(retries !== undefined && retries > 0) {
+        tags.push(<RetryChip key="retry" count={retries}/>);
+    }
+    if(dupeCheck !== undefined) {
+        tags.push(<DupeChip key="dupe" check={dupeCheck}/>)
+    }
+    if(transform !== undefined) {
+        tags.push(<TransformChip key="transform" check={transform}/>)
+    }
+    if(useCache !== undefined) {
+        tags.push(<CacheChip key="cache" check={useCache}/>)
+    }
+    if(tags.length > 0) {
+        contextHints.push(<HStack key="tags">{tags}</HStack>)
+    }
+    if(reason !== undefined) {
+        contextHints.push(<span key="reason">Reason - {reason}</span>);
+    }
+
     switch(queueStatus) {
         case QUEUE_STATUS_QUEUED:
             indicator = <TimelineIndicatorIconQueued {...timelineIconProps} />;
@@ -315,7 +358,9 @@ const QueueTimelineItem = (props: {queueState: PlayEventQueueStateChange<string>
                 disableUntil="md"
                 timeline
                 unmountOnExit>
+                <Stack>
                 <ErrorAlert error={error} />
+                </Stack>
             </MSCollapsible>
         )
     } else {
@@ -334,6 +379,7 @@ const QueueTimelineItem = (props: {queueState: PlayEventQueueStateChange<string>
                     <Timeline.Title>
                         {title}
                     </Timeline.Title>
+                    {contextHints.length > 0 ? <Timeline.Description><HStack separator={<Separator orientation="vertical" height="5"/>}>{contextHints}</HStack></Timeline.Description> : undefined}
                 </Timeline.Content>
             </Timeline.Item>
     );
diff --git a/src/core/Api.ts b/src/core/Api.ts
index d133ad5c..35676a3f 100644
--- a/src/core/Api.ts
+++ b/src/core/Api.ts
@@ -1,6 +1,6 @@
 import type { PickKeys } from "ts-essentials"
 import type { CompareOpKey, ComponentMinimalSelect } from "../backend/common/database/drizzle/drizzleTypes.ts"
-import type { ClientType, ComponentAuthType, MonitoringStatus } from "./Atomic.ts"
+import type { ClientType, ComponentAuthType, MonitoringStatus, QueueContext } from "./Atomic.ts"
 import type { SourceType } from "./Atomic.ts"
 import type { ComponentType, DateLike, ErrorLike, JsonPlayObject, PlayState, QueueName, Replace, SOURCE_SOT_TYPES, SourcePlayerJson } from "./Atomic.ts"
 import type { Dayjs } from "dayjs"
@@ -36,6 +36,7 @@ export interface QueueStateApi {
     error?: ErrorLike
     updatedAt: string
     createdAt: string
+    context?: QueueContext
 }
 
 export interface PlayApiCommonDetailed extends PlayApiCommon {
diff --git a/src/core/tests/utils/apiFixtures.ts b/src/core/tests/utils/apiFixtures.ts
index cd6c8e66..ef9429c5 100644
--- a/src/core/tests/utils/apiFixtures.ts
+++ b/src/core/tests/utils/apiFixtures.ts
@@ -14,6 +14,7 @@ import { CALCULATED_PLAYER_STATUSES } from '../../Atomic.ts';
 import { REPORTED_PLAYER_STATUSES } from '../../Atomic.ts';
 import { generateArray } from "../../DataUtils.ts";
 import type {ErrorIsh} from "../../ErrorUtils.ts";
+import { serializeError } from "serialize-error";
 
 export const generatePlayApiCommon = (commonData: Partial<PlayApiCommon> & {play?: JsonPlayObject | PlayObject } = {}, ...playOpts: Parameters<typeof generatePlay>): PlayApiCommon => {
     let play: JsonPlayObject | PlayObject;
@@ -102,7 +103,13 @@ export const generatePlayApiCommonDetailed = (opts: {
         input: inputRes,
         queueStates: [queueRes],
         error,
-        events: []
+        events: [
+            {eventName: 'queueStateChange', playId: 1, data: {queueName: 'ingress', queueStatus: 'queued', retries: 2,
+                error: serializeError(generateFakeError()),
+                 context: {reason: 'Bulk scrobble for dead Plays by system', dupeCheck: false, transform: true}}},
+            {eventName: 'playStateChange', playId: 1, data: {state: 'discarded', reason: 'Monitoring was off'}},
+            {eventName: 'queueStateChange', playId: 1, data: {queueName: 'ingress', retries: 1, queueStatus: 'failed', error: serializeError(generateFakeError())}},
+        ]
     }
 }