diff --git a/bot/src/main/java/org/openjdk/skara/bot/BotRunner.java b/bot/src/main/java/org/openjdk/skara/bot/BotRunner.java
index ae7a6dd96..eb2df0d32 100644
--- a/bot/src/main/java/org/openjdk/skara/bot/BotRunner.java
+++ b/bot/src/main/java/org/openjdk/skara/bot/BotRunner.java
@@ -58,7 +58,7 @@ enum TaskPhases {
         END
     }
 
-    private AtomicInteger workIdCounter = new AtomicInteger();
+    private final AtomicInteger workIdCounter = new AtomicInteger();
 
     private class RunnableWorkItem implements Runnable {
         private static final Counter.WithThreeLabels EXCEPTIONS_COUNTER =
@@ -71,6 +71,11 @@ private class RunnableWorkItem implements Runnable {
             Gauge.name("skara_runner_allocated_bytes").labels("bot", "work_item").register();
 
         private final WorkItem item;
+        private final int workId = workIdCounter.incrementAndGet();
+        private final Instant createTime = Instant.now();
+        // This gets updated by the watchdog when a timeout occurs to avoid
+        // repeating the timeout log messages too often.
+        private Instant timeoutWarningTime = createTime;
 
         RunnableWorkItem(WorkItem wrappedItem) {
             item = wrappedItem;
@@ -179,7 +184,7 @@ private void runMeasured() {
 
             Collection<WorkItem> followUpItems = null;
             try (var __ = new LogContext(Map.of("work_item", item.toString(),
-                    "work_id", String.valueOf(workIdCounter.incrementAndGet())))) {
+                    "work_id", String.valueOf(workId)))) {
                 log.log(Level.FINE, "Executing item " + item + " on repository " + scratchPath, TaskPhases.BEGIN);
                 try {
                     followUpItems = item.run(scratchPath);
@@ -225,8 +230,9 @@ private void runMeasured() {
 
                     if (maySubmit) {
                         pending.remove(candidate);
-                        executor.submit(new RunnableWorkItem(candidate));
-                        active.put(candidate, Instant.now());
+                        RunnableWorkItem runnableWorkItem = new RunnableWorkItem(candidate);
+                        executor.submit(runnableWorkItem);
+                        active.put(candidate, runnableWorkItem);
                         log.finer("Submitting candidate: " + candidate);
                     }
                 }
@@ -234,8 +240,10 @@ private void runMeasured() {
         }
     }
 
+    // Mapping of pending items to the active item preventing them from running
     private final Map<WorkItem, Optional<WorkItem>> pending;
-    private final Map<WorkItem, Instant> active;
+    // Mapping of active WorkItem to their RunnableWorkItem
+    private final Map<WorkItem, RunnableWorkItem> active;
     private final Deque<Path> scratchPaths;
 
     private static final Counter.WithTwoLabels SCHEDULED_COUNTER =
@@ -249,13 +257,13 @@ private void submitOrSchedule(WorkItem item) {
             for (var activeItem : active.keySet()) {
                 if (!activeItem.concurrentWith(item)) {
 
-                    for (var pendingItem : pending.entrySet()) {
+                    for (var pendingItem : pending.keySet()) {
                         // If there are pending items of the same type that we cannot run concurrently with, replace them.
-                        if (item.replaces(pendingItem.getKey())) {
-                            log.finer("Discarding obsoleted item " + pendingItem.getKey() +
+                        if (item.replaces(pendingItem)) {
+                            log.finer("Discarding obsoleted item " + pendingItem +
                                               " in favor of item " + item);
                             DISCARDED_COUNTER.labels(item.botName(), item.workItemName()).inc();
-                            pending.remove(pendingItem.getKey());
+                            pending.remove(pendingItem);
                             // There can't be more than one
                             break;
                         }
@@ -266,8 +274,9 @@ private void submitOrSchedule(WorkItem item) {
                 }
             }
 
-            executor.submit(new RunnableWorkItem(item));
-            active.put(item, Instant.now());
+            RunnableWorkItem runnableWorkItem = new RunnableWorkItem(item);
+            executor.submit(runnableWorkItem);
+            active.put(item, runnableWorkItem);
         }
     }
 
@@ -370,13 +379,14 @@ private void checkPeriodicItems() {
 
     private void itemWatchdog() {
         synchronized (executor) {
-            for (var activeItem : active.entrySet()) {
-                var activeDuration = Duration.between(activeItem.getValue(), Instant.now());
-                if (activeDuration.compareTo(watchdogWarnTimeout) > 0) {
-                    log.severe("Item " + activeItem.getKey() + " has been active more than " + activeDuration +
-                                       " - this may be an error!");
+            for (var activeRunnableItem : active.values()) {
+                Instant now = Instant.now();
+                var timeoutDuration = Duration.between(activeRunnableItem.timeoutWarningTime, now);
+                if (timeoutDuration.compareTo(watchdogWarnTimeout) > 0) {
+                    log.severe("Item " + activeRunnableItem.item + " with workId " + activeRunnableItem.workId + " has been active more than " +
+                            Duration.between(activeRunnableItem.createTime, now) + " - this may be an error!");
                     // Reset the counter to avoid continuous reporting - once every watchdogTimeout is enough
-                    activeItem.setValue(Instant.now());
+                    activeRunnableItem.timeoutWarningTime = now;
                 }
             }
             // Inform the global watchdog that the scheduler is still executing items