diff --git a/artifactory/commands/transferfiles/delayedartifactshandler.go b/artifactory/commands/transferfiles/delayedartifactshandler.go
index adab43f5c..11af1d3cb 100644
--- a/artifactory/commands/transferfiles/delayedartifactshandler.go
+++ b/artifactory/commands/transferfiles/delayedartifactshandler.go
@@ -161,6 +161,7 @@ func handleDelayedArtifactsFiles(filesToConsume []string, base phaseBase, delayU
 }
 
 func consumeDelayedArtifactsFiles(pcWrapper *producerConsumerWrapper, filesToConsume []string, uploadChunkChan chan UploadedChunk, base phaseBase, delayHelper delayUploadHelper, errorsChannelMng *ErrorsChannelMng) error {
+	log.Debug(fmt.Sprintf("Starting to handle delayed artifacts files. Found %d files.", len(filesToConsume)))
 	for _, filePath := range filesToConsume {
 		log.Debug("Handling delayed artifacts file: '" + filePath + "'")
 		delayedArtifactsFile, err := readDelayFile(filePath)
diff --git a/artifactory/commands/transferfiles/errorshandler.go b/artifactory/commands/transferfiles/errorshandler.go
index f67079039..db9a8cb3e 100644
--- a/artifactory/commands/transferfiles/errorshandler.go
+++ b/artifactory/commands/transferfiles/errorshandler.go
@@ -11,6 +11,7 @@ import (
 	"github.com/jfrog/jfrog-client-go/utils/io/fileutils"
 	"github.com/jfrog/jfrog-client-go/utils/log"
 	"os"
+	"path"
 	"time"
 )
 
@@ -189,7 +190,7 @@ func (mng *TransferErrorsMng) writeErrorContent(e ExtendedFileUploadStatusRespon
 }
 
 func (mng *TransferErrorsMng) writeSkippedErrorContent(e ExtendedFileUploadStatusResponse) error {
-	log.Debug(fmt.Sprintf("Writing '%s' to file %s", e.Reason, mng.errorWriterMng.skipped.filePath))
+	logWritingArtifact(e, mng.errorWriterMng.skipped.filePath)
 	mng.errorWriterMng.skipped.writer.Write(e)
 	mng.errorWriterMng.skipped.errorCount++
 	// If file contains maximum number of errors - create and write to a new errors file
@@ -213,7 +214,7 @@ func (mng *TransferErrorsMng) writeSkippedErrorContent(e ExtendedFileUploadStatu
 }
 
 func (mng *TransferErrorsMng) writeRetryableErrorContent(e ExtendedFileUploadStatusResponse) error {
-	log.Debug(fmt.Sprintf("Writing '%s' to file %s", e.Reason, mng.errorWriterMng.retryable.filePath))
+	logWritingArtifact(e, mng.errorWriterMng.retryable.filePath)
 	mng.errorWriterMng.retryable.writer.Write(e)
 	mng.errorWriterMng.retryable.errorCount++
 	// If file contains maximum number of errors - create and write to a new errors file
@@ -236,6 +237,17 @@ func (mng *TransferErrorsMng) writeRetryableErrorContent(e ExtendedFileUploadSta
 	return nil
 }
 
+func logWritingArtifact(e ExtendedFileUploadStatusResponse, errorsFilePath string) {
+	if log.GetLogger().GetLogLevel() != log.DEBUG {
+		return
+	}
+	msg := fmt.Sprintf("Writing artifact '%s' to errors file '%s'.", path.Join(e.Repo, e.Path, e.Name), errorsFilePath)
+	if e.Reason != "" {
+		msg += fmt.Sprintf(" Reason: '%s'.", e.Reason)
+	}
+	log.Debug(msg)
+}
+
 func (writerMng *errorWriter) closeWriter() error {
 	// Close content writer and move output file to our working directory
 	if writerMng.writer == nil {
diff --git a/artifactory/commands/transferfiles/manager.go b/artifactory/commands/transferfiles/manager.go
index 2b825f88b..e9904b592 100644
--- a/artifactory/commands/transferfiles/manager.go
+++ b/artifactory/commands/transferfiles/manager.go
@@ -228,6 +228,8 @@ func runProducerConsumers(pcWrapper *producerConsumerWrapper) (executionErr erro
 	go func() {
 		// Wait till notified that the builder has no additional tasks, and close the builder producer consumer.
 		<-pcWrapper.chunkBuilderProducerConsumer.GetFinishedNotification()
+		log.Debug("Chunk builder producer consumer has completed all tasks. " +
+			"All files relevant to this phase were found and added to chunks that are being uploaded...")
 		pcWrapper.chunkBuilderProducerConsumer.Done()
 	}()
 
@@ -261,6 +263,7 @@ func pollUploads(phaseBase *phaseBase, srcUpService *srcUserPluginService, uploa
 	}
 	for i := 0; ; i++ {
 		if ShouldStop(phaseBase, nil, errorsChannelMng) {
+			log.Debug("Stop signal received while polling on uploads...")
 			return
 		}
 		time.Sleep(waitTimeBetweenChunkStatusSeconds * time.Second)
@@ -284,6 +287,7 @@ func pollUploads(phaseBase *phaseBase, srcUpService *srcUserPluginService, uploa
 		// it will be written to the error channel
 		if chunksLifeCycleManager.totalChunks == 0 {
 			if shouldStopPolling(doneChan) {
+				log.Debug("Stopping to poll on uploads...")
 				return
 			}
 			continue
@@ -386,6 +390,7 @@ func handleChunksStatuses(phase *phaseBase, chunksStatus *api.UploadChunksStatus
 			stopped := handleFilesOfCompletedChunk(chunk.Files, errorsChannelMng)
 			// In case an error occurred while writing errors status's to the errors file - stop transferring.
 			if stopped {
+				log.Debug("Stop signal received while handling chunks statuses...")
 				return true
 			}
 			err = setChunkCompletedInRepoSnapshot(phase.stateManager, chunk.Files)