diff --git a/shared/packages/expectationManager/src/expectationTracker/lib/trackedExpectationAPI.ts b/shared/packages/expectationManager/src/expectationTracker/lib/trackedExpectationAPI.ts
index 66eaf92c..5995b4ff 100644
--- a/shared/packages/expectationManager/src/expectationTracker/lib/trackedExpectationAPI.ts
+++ b/shared/packages/expectationManager/src/expectationTracker/lib/trackedExpectationAPI.ts
@@ -187,7 +187,15 @@ export class TrackedExpectationAPI {
 			noAssignedWorkerReason = trackedExp.session.noAssignedWorkerReason
 		}
 
-		if (!trackedExp.noWorkerAssignedTime) trackedExp.noWorkerAssignedTime = Date.now()
+		if (!trackedExp.noWorkerAssignedTime) {
+			const now = Date.now()
+			this.logger.error(
+				`Setting trackedExp.noWorkerAssignedTime of "${expLabel(trackedExp)}" to ${now} (reason: ${
+					noAssignedWorkerReason.tech
+				})`
+			)
+			trackedExp.noWorkerAssignedTime = now
+		}
 
 		// Special case: When WAITING and no worker was assigned, return to NEW so that another worker might be assigned:
 		if (trackedExp.state === ExpectedPackageStatusAPI.WorkStatusState.WAITING) {
diff --git a/shared/packages/expectationManager/src/internalManager/lib/trackedWorkerAgents.ts b/shared/packages/expectationManager/src/internalManager/lib/trackedWorkerAgents.ts
index 88ee2513..6ab38f0e 100644
--- a/shared/packages/expectationManager/src/internalManager/lib/trackedWorkerAgents.ts
+++ b/shared/packages/expectationManager/src/internalManager/lib/trackedWorkerAgents.ts
@@ -174,7 +174,11 @@ export class TrackedWorkerAgents {
 	public async assignWorkerToSession(trackedExp: TrackedExpectation): Promise<void> {
 		const session: ExpectationStateHandlerSession | null = trackedExp.session
 		if (!session) throw new Error('ExpectationManager: Internal error: Session not set')
-		if (session.assignedWorker) return // A worker has already been assigned
+		if (session.assignedWorker) {
+			// A worker has already been assigned
+			trackedExp.noWorkerAssignedTime = null
+			return
+		}
 
 		if (!trackedExp.availableWorkers.size) {
 			session.noAssignedWorkerReason = { user: `No workers available`, tech: `No workers available` }