diff --git a/pkg/distributor/distributor.go b/pkg/distributor/distributor.go
index 9997b637f1..d57d813f1f 100644
--- a/pkg/distributor/distributor.go
+++ b/pkg/distributor/distributor.go
@@ -227,7 +227,7 @@ func (d *Distributor) Push(ctx context.Context, req *logproto.PushRequest) (*log
 	validatedSamplesSize := 0
 	validatedSamplesCount := 0
 
-	validationContext := d.validator.getValidationContextFor(userID)
+	validationContext := d.validator.getValidationContextForTime(time.Now(), userID)
 
 	for _, stream := range req.Streams {
 		// Truncate first so subsequent steps have consistent line lengths
diff --git a/pkg/distributor/distributor_test.go b/pkg/distributor/distributor_test.go
index 7eeb8d5389..77b7a93975 100644
--- a/pkg/distributor/distributor_test.go
+++ b/pkg/distributor/distributor_test.go
@@ -146,7 +146,7 @@ func Benchmark_SortLabelsOnPush(b *testing.B) {
 	d := prepare(&testing.T{}, limits, nil, func(addr string) (ring_client.PoolClient, error) { return ingester, nil })
 	defer services.StopAndAwaitTerminated(context.Background(), d) //nolint:errcheck
 	request := makeWriteRequest(10, 10)
-	vCtx := d.validator.getValidationContextFor("123")
+	vCtx := d.validator.getValidationContextForTime(testTime, "123")
 	for n := 0; n < b.N; n++ {
 		stream := request.Streams[0]
 		stream.Labels = `{buzz="f", a="b"}`
diff --git a/pkg/distributor/validator.go b/pkg/distributor/validator.go
index c279c74625..f69dc5c18e 100644
--- a/pkg/distributor/validator.go
+++ b/pkg/distributor/validator.go
@@ -13,6 +13,10 @@ import (
 	"github.com/grafana/loki/pkg/validation"
 )
 
+const (
+	timeFormat = time.RFC3339
+)
+
 type Validator struct {
 	Limits
 }
@@ -39,8 +43,7 @@ type validationContext struct {
 	userID string
 }
 
-func (v Validator) getValidationContextFor(userID string) validationContext {
-	now := time.Now()
+func (v Validator) getValidationContextForTime(now time.Time, userID string) validationContext {
 	return validationContext{
 		userID:                 userID,
 		rejectOldSample:        v.RejectOldSamples(userID),
@@ -57,16 +60,21 @@ func (v Validator) getValidationContextFor(userID string) validationContext {
 // ValidateEntry returns an error if the entry is invalid
 func (v Validator) ValidateEntry(ctx validationContext, labels string, entry logproto.Entry) error {
 	ts := entry.Timestamp.UnixNano()
+
+	// Makes time string on the error message formatted consistently.
+	formatedEntryTime := entry.Timestamp.Format(timeFormat)
+	formatedRejectMaxAgeTime := time.Unix(0, ctx.rejectOldSampleMaxAge).Format(timeFormat)
+
 	if ctx.rejectOldSample && ts < ctx.rejectOldSampleMaxAge {
 		validation.DiscardedSamples.WithLabelValues(validation.GreaterThanMaxSampleAge, ctx.userID).Inc()
 		validation.DiscardedBytes.WithLabelValues(validation.GreaterThanMaxSampleAge, ctx.userID).Add(float64(len(entry.Line)))
-		return httpgrpc.Errorf(http.StatusBadRequest, validation.GreaterThanMaxSampleAgeErrorMsg, labels, entry.Timestamp)
+		return httpgrpc.Errorf(http.StatusBadRequest, validation.GreaterThanMaxSampleAgeErrorMsg, labels, formatedEntryTime, formatedRejectMaxAgeTime)
 	}
 
 	if ts > ctx.creationGracePeriod {
 		validation.DiscardedSamples.WithLabelValues(validation.TooFarInFuture, ctx.userID).Inc()
 		validation.DiscardedBytes.WithLabelValues(validation.TooFarInFuture, ctx.userID).Add(float64(len(entry.Line)))
-		return httpgrpc.Errorf(http.StatusBadRequest, validation.TooFarInFutureErrorMsg, labels, entry.Timestamp)
+		return httpgrpc.Errorf(http.StatusBadRequest, validation.TooFarInFutureErrorMsg, labels, formatedEntryTime)
 	}
 
 	if maxSize := ctx.maxLineSize; maxSize != 0 && len(entry.Line) > maxSize {
diff --git a/pkg/distributor/validator_test.go b/pkg/distributor/validator_test.go
index af3625e347..1426cfc681 100644
--- a/pkg/distributor/validator_test.go
+++ b/pkg/distributor/validator_test.go
@@ -59,14 +59,20 @@ func TestValidator_ValidateEntry(t *testing.T) {
 				},
 			},
 			logproto.Entry{Timestamp: testTime.Add(-time.Hour * 5), Line: "test"},
-			httpgrpc.Errorf(http.StatusBadRequest, validation.GreaterThanMaxSampleAgeErrorMsg, testStreamLabels, testTime.Add(-time.Hour*5)),
+			httpgrpc.Errorf(
+				http.StatusBadRequest,
+				validation.GreaterThanMaxSampleAgeErrorMsg,
+				testStreamLabels,
+				testTime.Add(-time.Hour*5).Format(timeFormat),
+				testTime.Add(-1*time.Hour).Format(timeFormat), // same as RejectOldSamplesMaxAge
+			),
 		},
 		{
 			"test too new",
 			"test",
 			nil,
 			logproto.Entry{Timestamp: testTime.Add(time.Hour * 5), Line: "test"},
-			httpgrpc.Errorf(http.StatusBadRequest, validation.TooFarInFutureErrorMsg, testStreamLabels, testTime.Add(time.Hour*5)),
+			httpgrpc.Errorf(http.StatusBadRequest, validation.TooFarInFutureErrorMsg, testStreamLabels, testTime.Add(time.Hour*5).Format(timeFormat)),
 		},
 		{
 			"line too long",
@@ -89,7 +95,7 @@ func TestValidator_ValidateEntry(t *testing.T) {
 			v, err := NewValidator(o)
 			assert.NoError(t, err)
 
-			err = v.ValidateEntry(v.getValidationContextFor(tt.userID), testStreamLabels, tt.entry)
+			err = v.ValidateEntry(v.getValidationContextForTime(testTime, tt.userID), testStreamLabels, tt.entry)
 			assert.Equal(t, tt.expected, err)
 		})
 	}
@@ -190,7 +196,7 @@ func TestValidator_ValidateLabels(t *testing.T) {
 			v, err := NewValidator(o)
 			assert.NoError(t, err)
 
-			err = v.ValidateLabels(v.getValidationContextFor(tt.userID), mustParseLabels(tt.labels), logproto.Stream{Labels: tt.labels})
+			err = v.ValidateLabels(v.getValidationContextForTime(testTime, tt.userID), mustParseLabels(tt.labels), logproto.Stream{Labels: tt.labels})
 			assert.Equal(t, tt.expected, err)
 		})
 	}
diff --git a/pkg/validation/validate.go b/pkg/validation/validate.go
index d8fb7903af..e38f1bd337 100644
--- a/pkg/validation/validate.go
+++ b/pkg/validation/validate.go
@@ -34,7 +34,7 @@ const (
 	TooFarBehind    = "too_far_behind"
 	// GreaterThanMaxSampleAge is a reason for discarding log lines which are older than the current time - `reject_old_samples_max_age`
 	GreaterThanMaxSampleAge         = "greater_than_max_sample_age"
-	GreaterThanMaxSampleAgeErrorMsg = "entry for stream '%s' has timestamp too old: %v"
+	GreaterThanMaxSampleAgeErrorMsg = "entry for stream '%s' has timestamp too old: %v, oldest acceptable timestamp is: %v"
 	// TooFarInFuture is a reason for discarding log lines which are newer than the current time + `creation_grace_period`
 	TooFarInFuture         = "too_far_in_future"
 	TooFarInFutureErrorMsg = "entry for stream '%s' has timestamp too new: %v"