diff --git a/packages/cli/src/modules/insights/__tests__/insights-compaction.service.test.ts b/packages/cli/src/modules/insights/__tests__/insights-compaction.service.test.ts
index 842f1e2515..2d7c73338e 100644
--- a/packages/cli/src/modules/insights/__tests__/insights-compaction.service.test.ts
+++ b/packages/cli/src/modules/insights/__tests__/insights-compaction.service.test.ts
@@ -282,11 +282,11 @@ describe('compaction', () => {
 			const workflow = await createWorkflow({}, project);
 
 			// create 100 more events than the batch size (500)
-			const batchSize = 600;
+			const numberOfEvents = 600;
 
 			let timestamp = DateTime.utc().startOf('hour');
 			const events = Array<{ type: 'success'; value: number; timestamp: DateTime }>();
-			for (let i = 0; i < batchSize; i++) {
+			for (let i = 0; i < numberOfEvents; i++) {
 				events.push({ type: 'success', value: 1, timestamp });
 				timestamp = timestamp.plus({ minute: 1 });
 			}
@@ -296,13 +296,13 @@ describe('compaction', () => {
 			await insightsCompactionService.compactInsights();
 
 			// ASSERT
-			// compaction batch size is 500, so rawToHour should be called 3 times:
-			// 1st call: 500 events, 2nd call: 100 events, and third call that returns nothing
-			expect(rawToHourSpy).toHaveBeenCalledTimes(3);
+			// compaction batch size is 500, so rawToHour should be called 2 times:
+			// 1st call: 500 events, 2nd call: 100 events
+			expect(rawToHourSpy).toHaveBeenCalledTimes(2);
 			await expect(insightsRawRepository.count()).resolves.toBe(0);
 			const allCompacted = await insightsByPeriodRepository.find({ order: { periodStart: 1 } });
 			const accumulatedValues = allCompacted.reduce((acc, event) => acc + event.value, 0);
-			expect(accumulatedValues).toBe(batchSize);
+			expect(accumulatedValues).toBe(numberOfEvents);
 		});
 	});
 
diff --git a/packages/cli/src/modules/insights/insights-collection.service.ts b/packages/cli/src/modules/insights/insights-collection.service.ts
index eb65cdfe01..409b575fcd 100644
--- a/packages/cli/src/modules/insights/insights-collection.service.ts
+++ b/packages/cli/src/modules/insights/insights-collection.service.ts
@@ -100,6 +100,7 @@ export class InsightsCollectionService {
 
 		// Wait for all in-progress asynchronous flushes
 		// Flush any remaining events
+		this.logger.debug('Flushing remaining insights before shutdown');
 		await Promise.all([...this.flushesInProgress, this.flushEvents()]);
 	}
 
@@ -144,18 +145,21 @@ export class InsightsCollectionService {
 		}
 
 		if (!this.isAsynchronouslySavingInsights) {
+			this.logger.debug('Flushing insights synchronously (shutdown in progress)');
 			// If we are not asynchronously saving insights, we need to flush the events
 			await this.flushEvents();
 		}
 
 		// If the buffer is full, flush the events asynchronously
 		if (this.bufferedInsights.size >= this.insightsConfig.flushBatchSize) {
+			this.logger.debug(`Buffer is full (${this.bufferedInsights.size} insights), flushing events`);
 			// Fire and forget flush to avoid blocking the workflow execute after handler
 			void this.flushEvents();
 		}
 	}
 
 	private async saveInsightsMetadataAndRaw(insightsRawToInsertBuffer: Set<BufferedInsight>) {
+		this.logger.debug(`Flushing ${insightsRawToInsertBuffer.size} insights`);
 		const workflowIdNames: Map<string, string> = new Map();
 
 		for (const event of insightsRawToInsertBuffer) {
@@ -188,6 +192,7 @@ export class InsightsCollectionService {
 			return acc;
 		}, [] as InsightsMetadata[]);
 
+		this.logger.debug(`Saving ${metadataToUpsert.length} insights metadata for workflows`);
 		await this.insightsMetadataRepository.upsert(metadataToUpsert, ['workflowId']);
 
 		const upsertMetadata = await this.insightsMetadataRepository.findBy({
@@ -215,6 +220,7 @@ export class InsightsCollectionService {
 			events.push(insight);
 		}
 
+		this.logger.debug(`Inserting ${events.length} insights raw`);
 		await this.insightsRawRepository.insert(events);
 	}
 
diff --git a/packages/cli/src/modules/insights/insights-compaction.service.ts b/packages/cli/src/modules/insights/insights-compaction.service.ts
index 47c852d864..4061849deb 100644
--- a/packages/cli/src/modules/insights/insights-compaction.service.ts
+++ b/packages/cli/src/modules/insights/insights-compaction.service.ts
@@ -44,21 +44,27 @@ export class InsightsCompactionService {
 
 		// Compact raw data to hourly aggregates
 		do {
+			this.logger.debug('Compacting raw data to hourly aggregates');
 			numberOfCompactedRawData = await this.compactRawToHour();
-		} while (numberOfCompactedRawData > 0);
+			this.logger.debug(`Compacted ${numberOfCompactedRawData} raw data to hourly aggregates`);
+		} while (numberOfCompactedRawData === this.insightsConfig.compactionBatchSize);
 
 		let numberOfCompactedHourData: number;
 
 		// Compact hourly data to daily aggregates
 		do {
+			this.logger.debug('Compacting hourly data to daily aggregates');
 			numberOfCompactedHourData = await this.compactHourToDay();
-		} while (numberOfCompactedHourData > 0);
+			this.logger.debug(`Compacted ${numberOfCompactedHourData} hourly data to daily aggregates`);
+		} while (numberOfCompactedHourData === this.insightsConfig.compactionBatchSize);
 
 		let numberOfCompactedDayData: number;
 		// Compact daily data to weekly aggregates
 		do {
+			this.logger.debug('Compacting daily data to weekly aggregates');
 			numberOfCompactedDayData = await this.compactDayToWeek();
-		} while (numberOfCompactedDayData > 0);
+			this.logger.debug(`Compacted ${numberOfCompactedDayData} daily data to weekly aggregates`);
+		} while (numberOfCompactedDayData === this.insightsConfig.compactionBatchSize);
 	}
 
 	/**