diff --git a/go/vt/mysqlctl/builtinbackupengine.go b/go/vt/mysqlctl/builtinbackupengine.go
index 0beb83036ee..bf40fdad8d5 100644
--- a/go/vt/mysqlctl/builtinbackupengine.go
+++ b/go/vt/mysqlctl/builtinbackupengine.go
@@ -613,7 +613,15 @@ func (be *BuiltinBackupEngine) backupFiles(
 	wg := sync.WaitGroup{}
 
 	ctxCancel, cancel := context.WithCancel(ctx)
-	defer cancel()
+	defer func() {
+		// We may still have operations in flight that require a valid context, such as adding files to S3.
+		// Unless we encountered an error, we should not cancel the context. This is taken care of later
+		// in the process. If we encountered an error however, we can safely cancel the context as we should
+		// no longer work on anything and exit fast.
+		if finalErr != nil {
+			cancel()
+		}
+	}()
 
 	for i := range fes {
 		wg.Add(1)
@@ -634,7 +642,7 @@ func (be *BuiltinBackupEngine) backupFiles(
 			// We check for errors before checking if the context is canceled on purpose, if there was an
 			// error, the context would have been canceled already.
 			if bh.HasErrors() {
-				params.Logger.Errorf("Failed to restore files due to error: %v", bh.Error())
+				params.Logger.Errorf("Failed to backup files due to error: %v", bh.Error())
 				return
 			}
 
@@ -811,12 +819,15 @@ func (bp *backupPipe) ReportProgress(ctx context.Context, period time.Duration,
 
 // backupFile backs up an individual file.
 func (be *BuiltinBackupEngine) backupFile(ctx context.Context, params BackupParams, bh backupstorage.BackupHandle, fe *FileEntry, name string) (finalErr error) {
-	ctx, cancel := context.WithCancel(ctx)
-	defer func() {
-		if finalErr != nil {
-			cancel()
-		}
-	}()
+	// We need another context that does not live outside of this function.
+	// Reporting progress, compressing and writing are operations that will be
+	// over by the time we exit this function, they can use this cancelable context.
+	// However, AddFile is something that may continue in the background even after
+	// this function exits. In this case, we give it the parent context so the caller
+	// has more control over when to cancel AddFile.
+	cancelableCtx, cancel := context.WithCancel(ctx)
+	defer cancel()
+
 	// Open the source file for reading.
 	openSourceAt := time.Now()
 	source, err := fe.open(params.Cnf, true)
@@ -841,7 +852,7 @@ func (be *BuiltinBackupEngine) backupFile(ctx context.Context, params BackupPara
 
 	attemptStr := attemptToString(fe.AttemptNb)
 	br := newBackupReader(fe.Name, fi.Size(), timedSource)
-	go br.ReportProgress(ctx, builtinBackupProgress, params.Logger, false /*restore*/, attemptStr)
+	go br.ReportProgress(cancelableCtx, builtinBackupProgress, params.Logger, false /*restore*/, attemptStr)
 
 	// Open the destination file for writing, and a buffer.
 	params.Logger.Infof("Backing up file: %v %s", fe.Name, attemptStr)
@@ -889,7 +900,7 @@ func (be *BuiltinBackupEngine) backupFile(ctx context.Context, params BackupPara
 		if backupStorageCompress {
 			var compressor io.WriteCloser
 			if ExternalCompressorCmd != "" {
-				compressor, err = newExternalCompressor(ctx, ExternalCompressorCmd, writer, params.Logger)
+				compressor, err = newExternalCompressor(cancelableCtx, ExternalCompressorCmd, writer, params.Logger)
 			} else {
 				compressor, err = newBuiltinCompressor(CompressionEngineName, writer, params.Logger)
 			}
@@ -900,7 +911,7 @@ func (be *BuiltinBackupEngine) backupFile(ctx context.Context, params BackupPara
 			compressStats := params.Stats.Scope(stats.Operation("Compressor:Write"))
 			writer = ioutil.NewMeteredWriter(compressor, compressStats.TimedIncrementBytes)
 
-			closer := ioutil.NewTimeoutCloser(ctx, compressor, closeTimeout)
+			closer := ioutil.NewTimeoutCloser(cancelableCtx, compressor, closeTimeout)
 			defer func() {
 				// Close gzip to flush it, after that all data is sent to writer.
 				closeCompressorAt := time.Now()