diff --git a/pkg/cli/tsdump_test.go b/pkg/cli/tsdump_test.go
index 837c1810b8c1..8e4969850c34 100644
--- a/pkg/cli/tsdump_test.go
+++ b/pkg/cli/tsdump_test.go
@@ -164,7 +164,7 @@ func parseDDInput(t *testing.T, input string, w *datadogWriter) {
 			(data != nil && data.Metric != metricName ||
 				(data != nil && source != nameValueTimestamp[1])) {
 			if data != nil {
-				err := w.emitDataDogMetrics([]DatadogSeries{*data})
+				_, err := w.emitDataDogMetrics([]DatadogSeries{*data})
 				require.NoError(t, err)
 			}
 			data = &DatadogSeries{
@@ -182,7 +182,7 @@ func parseDDInput(t *testing.T, input string, w *datadogWriter) {
 			Timestamp: ts,
 		})
 	}
-	err := w.emitDataDogMetrics([]DatadogSeries{*data})
+	_, err := w.emitDataDogMetrics([]DatadogSeries{*data})
 	require.NoError(t, err)
 }
 
diff --git a/pkg/cli/tsdump_upload.go b/pkg/cli/tsdump_upload.go
index 936bfbe60c1b..806e69e58aca 100644
--- a/pkg/cli/tsdump_upload.go
+++ b/pkg/cli/tsdump_upload.go
@@ -37,6 +37,10 @@ const (
 	DatadogSeriesTypeRate
 	DatadogSeriesTypeGauge
 )
+const (
+	UploadStatusSuccess = "Success"
+	UploadStatusFailure = "Failed"
+)
 
 var (
 	// each site in datadog has a different host name. ddSiteToHostMap
@@ -207,12 +211,14 @@ func dump(kv *roachpb.KeyValue) (*DatadogSeries, error) {
 
 var printLock syncutil.Mutex
 
-func (d *datadogWriter) emitDataDogMetrics(data []DatadogSeries) error {
+func (d *datadogWriter) emitDataDogMetrics(data []DatadogSeries) ([]string, error) {
 	tags := getUploadTags(d)
 
+	emittedMetrics := make([]string, len(data))
 	for i := 0; i < len(data); i++ {
 		data[i].Tags = append(data[i].Tags, tags...)
 		data[i].Metric = d.namePrefix + data[i].Metric
+		emittedMetrics[i] = data[i].Metric
 	}
 
 	// When running in init mode, we insert zeros with the current
@@ -242,7 +248,7 @@ func (d *datadogWriter) emitDataDogMetrics(data []DatadogSeries) error {
 		)
 	}()
 
-	return d.flush(data)
+	return emittedMetrics, d.flush(data)
 }
 
 func getUploadTags(d *datadogWriter) []string {
@@ -294,7 +300,8 @@ func (d *datadogWriter) flush(data []DatadogSeries) error {
 	}
 
 	retryOpts := base.DefaultRetryOptions()
-	retryOpts.MaxRetries = 5
+	retryOpts.MaxBackoff = 2 * time.Second
+	retryOpts.MaxRetries = 100
 	var req *http.Request
 	for retry := retry.Start(retryOpts); retry.Next(); {
 		req, err = http.NewRequest("POST", d.targetURL, &zipBuf)
@@ -344,12 +351,20 @@ func (d *datadogWriter) upload(fileName string) error {
 	var wg sync.WaitGroup
 	ch := make(chan []DatadogSeries, 4000)
 
-	// errorsInDDUpload wraps the error collection in a mutex since
+	// metricsUploadState wraps the failed metrics collection in a mutex since
 	// they're collected concurrently.
-	var errorsInDDUpload struct {
+	var metricsUploadState struct {
 		syncutil.Mutex
-		errors []string
+		// we are taking map here as we want unique metric names which were failed across all tsdump upload requests.
+		uploadFailedMetrics     map[string]struct{}
+		isSingleUploadSucceeded bool
 	}
+	metricsUploadState.uploadFailedMetrics = make(map[string]struct{})
+	metricsUploadState.isSingleUploadSucceeded = false
+
+	markSuccessOnce := sync.OnceFunc(func() {
+		metricsUploadState.isSingleUploadSucceeded = true
+	})
 
 	// Note(davidh): This was previously set at 1000 and we'd get regular
 	// 400s from Datadog with the cryptic `Unable to decompress payload`
@@ -358,16 +373,19 @@ func (d *datadogWriter) upload(fileName string) error {
 	for i := 0; i < 10; i++ {
 		go func() {
 			for data := range ch {
-				err := d.emitDataDogMetrics(data)
+				emittedMetrics, err := d.emitDataDogMetrics(data)
 				if err != nil {
 					func() {
-						errorsInDDUpload.Lock()
-						defer errorsInDDUpload.Unlock()
-						errorsInDDUpload.errors = append(errorsInDDUpload.errors,
-							fmt.Sprintf("retries exhausted for datadog upload for series %s with error %v\n", data[0].Metric, err))
+						metricsUploadState.Lock()
+						defer metricsUploadState.Unlock()
+						for _, metric := range emittedMetrics {
+							metricsUploadState.uploadFailedMetrics[metric] = struct{}{}
+						}
+					}()
+				} else {
+					func() {
+						markSuccessOnce()
 					}()
-					wg.Done()
-					return
 				}
 				wg.Done()
 			}
@@ -394,11 +412,35 @@ func (d *datadogWriter) upload(fileName string) error {
 	year, month, day := d.uploadTime.Date()
 	dashboardLink := fmt.Sprintf(datadogDashboardURLFormat, debugTimeSeriesDumpOpts.clusterLabel, d.uploadID, day, int(month), year, fromUnixTimestamp, toUnixTimestamp)
 
-	if len(errorsInDDUpload.errors) != 0 {
-		fmt.Printf("\n%d upload errors occurred:\n%s\n", len(errorsInDDUpload.errors), strings.Join(errorsInDDUpload.errors, "\n"))
+	var uploadStatus string
+	if metricsUploadState.isSingleUploadSucceeded {
+		uploadStatus = UploadStatusSuccess
+	} else {
+		uploadStatus = UploadStatusFailure
+	}
+	fmt.Printf("\nUpload status: %s!\n", uploadStatus)
+
+	if metricsUploadState.isSingleUploadSucceeded {
+		if len(metricsUploadState.uploadFailedMetrics) != 0 {
+			fmt.Printf("The Tsdump upload to Datadog succeeded but %d metrics partially failed to upload."+
+				" These failures can be due to transietnt network errors. If any of these metrics are critical for your investigation,"+
+				" please re-upload the Tsdump:\n%s\n", len(metricsUploadState.uploadFailedMetrics), strings.Join(func() []string {
+				var failedMetricsList []string
+				index := 1
+				for metric := range metricsUploadState.uploadFailedMetrics {
+					metric = fmt.Sprintf("%d) %s", index, metric)
+					failedMetricsList = append(failedMetricsList, metric)
+					index++
+				}
+				return failedMetricsList
+			}(), "\n"))
+		}
+
+		fmt.Println("\nupload id: ", d.uploadID)
+		fmt.Printf("datadog dashboard link: %s\n", dashboardLink)
+	} else {
+		fmt.Println("All metric upload is failed. Please re-upload the Tsdump.")
 	}
-	fmt.Println("\nupload id:", d.uploadID)
-	fmt.Printf("datadog dashboard link: %s\n", dashboardLink)
 
 	close(ch)
 	return nil