diff --git a/cmd/prometheus/main.go b/cmd/prometheus/main.go
index 52c038238679..2d2df7630331 100644
--- a/cmd/prometheus/main.go
+++ b/cmd/prometheus/main.go
@@ -397,9 +397,6 @@ func main() {
 	agentOnlyFlag(a, "storage.agent.no-lockfile", "Do not create lockfile in data directory.").
 		Default("false").BoolVar(&cfg.agent.NoLockfile)
 
-	agentOnlyFlag(a, "storage.agent.reject-out-of-order-samples", "Reject out-of-order samples.").
-		Default("false").BoolVar(&cfg.agent.RejectOOOSamples)
-
 	a.Flag("storage.remote.flush-deadline", "How long to wait flushing sample on shutdown or config reload.").
 		Default("1m").PlaceHolder("<duration>").SetValue(&cfg.RemoteFlushDeadline)
 
@@ -1183,6 +1180,7 @@ func main() {
 	if agentMode {
 		// WAL storage.
 		opts := cfg.agent.ToAgentOptions()
+		opts.SetOutOfOrderTimeWindow(cfg.tsdb.OutOfOrderTimeWindow)
 		cancel := make(chan struct{})
 		g.Add(
 			func() error {
@@ -1712,6 +1710,7 @@ type agentOptions struct {
 	MinWALTime, MaxWALTime model.Duration
 	NoLockfile             bool
 	RejectOOOSamples       bool
+	OutOfOrderTimeWindow   int64
 }
 
 func (opts agentOptions) ToAgentOptions() agent.Options {
@@ -1723,7 +1722,6 @@ func (opts agentOptions) ToAgentOptions() agent.Options {
 		MinWALTime:        durationToInt64Millis(time.Duration(opts.MinWALTime)),
 		MaxWALTime:        durationToInt64Millis(time.Duration(opts.MaxWALTime)),
 		NoLockfile:        opts.NoLockfile,
-		RejectOOOSamples:  opts.RejectOOOSamples,
 	}
 }
 
diff --git a/docs/command-line/prometheus.md b/docs/command-line/prometheus.md
index a5c9ac9daaf4..93eaf251d0b7 100644
--- a/docs/command-line/prometheus.md
+++ b/docs/command-line/prometheus.md
@@ -41,7 +41,6 @@ The Prometheus monitoring server
 | <code class="text-nowrap">--storage.agent.retention.min-time</code> | Minimum age samples may be before being considered for deletion when the WAL is truncated Use with agent mode only. |  |
 | <code class="text-nowrap">--storage.agent.retention.max-time</code> | Maximum age samples may be before being forcibly deleted when the WAL is truncated Use with agent mode only. |  |
 | <code class="text-nowrap">--storage.agent.no-lockfile</code> | Do not create lockfile in data directory. Use with agent mode only. | `false` |
-| <code class="text-nowrap">--storage.agent.reject-out-of-order-samples</code> | Reject out-of-order samples. Use with agent mode only. | `false` |
 | <code class="text-nowrap">--storage.remote.flush-deadline</code> | How long to wait flushing sample on shutdown or config reload. | `1m` |
 | <code class="text-nowrap">--storage.remote.read-sample-limit</code> | Maximum overall number of samples to return via the remote read interface, in a single query. 0 means no limit. This limit is ignored for streamed response types. Use with server mode only. | `5e7` |
 | <code class="text-nowrap">--storage.remote.read-concurrent-limit</code> | Maximum number of concurrent remote read calls. 0 means no limit. Use with server mode only. | `10` |
diff --git a/tsdb/agent/db.go b/tsdb/agent/db.go
index 41bac430ee69..1fc7b3b42536 100644
--- a/tsdb/agent/db.go
+++ b/tsdb/agent/db.go
@@ -82,22 +82,29 @@ type Options struct {
 	// NoLockfile disables creation and consideration of a lock file.
 	NoLockfile bool
 
-	// RejectOOOSamples enables rejecting out of order samples.
-	RejectOOOSamples bool
+	// OutOfOrderTimeWindow specifies how much out of order is allowed, if any.
+	OutOfOrderTimeWindow int64
+}
+
+func (o *Options) SetOutOfOrderTimeWindow(outOfOrderTimeWindow int64) {
+	if outOfOrderTimeWindow < 0 {
+		return
+	}
+	o.OutOfOrderTimeWindow = outOfOrderTimeWindow
 }
 
 // DefaultOptions used for the WAL storage. They are reasonable for setups using
 // millisecond-precision timestamps.
 func DefaultOptions() *Options {
 	return &Options{
-		WALSegmentSize:    wlog.DefaultSegmentSize,
-		WALCompression:    wlog.CompressionNone,
-		StripeSize:        tsdb.DefaultStripeSize,
-		TruncateFrequency: DefaultTruncateFrequency,
-		MinWALTime:        DefaultMinWALTime,
-		MaxWALTime:        DefaultMaxWALTime,
-		NoLockfile:        false,
-		RejectOOOSamples:  false,
+		WALSegmentSize:       wlog.DefaultSegmentSize,
+		WALCompression:       wlog.CompressionNone,
+		StripeSize:           tsdb.DefaultStripeSize,
+		TruncateFrequency:    DefaultTruncateFrequency,
+		MinWALTime:           DefaultMinWALTime,
+		MaxWALTime:           DefaultMaxWALTime,
+		NoLockfile:           false,
+		OutOfOrderTimeWindow: 0,
 	}
 }
 
@@ -816,7 +823,7 @@ func (a *appender) Append(ref storage.SeriesRef, l labels.Labels, t int64, v flo
 	series.Lock()
 	defer series.Unlock()
 
-	if a.opts.RejectOOOSamples && t < series.lastTs {
+	if t <= a.minTs(series.lastTs) {
 		a.metrics.totalOutOfOrderSamples.Inc()
 		return 0, storage.ErrOutOfOrderSample
 	}
@@ -944,7 +951,7 @@ func (a *appender) AppendHistogram(ref storage.SeriesRef, l labels.Labels, t int
 	series.Lock()
 	defer series.Unlock()
 
-	if a.opts.RejectOOOSamples && t < series.lastTs {
+	if t <= a.minTs(series.lastTs) {
 		a.metrics.totalOutOfOrderSamples.Inc()
 		return 0, storage.ErrOutOfOrderSample
 	}
@@ -1117,3 +1124,13 @@ func (a *appender) logSeries() error {
 
 	return nil
 }
+
+// mintTs returns the minimum timestamp that a sample can have
+// and is needed for preventing underflow.
+func (a *appender) minTs(lastTs int64) int64 {
+	if lastTs < math.MinInt64+a.opts.OutOfOrderTimeWindow {
+		return math.MinInt64
+	}
+
+	return lastTs - a.opts.OutOfOrderTimeWindow
+}
diff --git a/tsdb/agent/db_test.go b/tsdb/agent/db_test.go
index 1029bcea7c54..267ae63b3706 100644
--- a/tsdb/agent/db_test.go
+++ b/tsdb/agent/db_test.go
@@ -16,6 +16,7 @@ package agent
 import (
 	"context"
 	"fmt"
+	"math"
 	"path/filepath"
 	"strconv"
 	"testing"
@@ -761,7 +762,9 @@ func TestDBAllowOOOSamples(t *testing.T) {
 	)
 
 	reg := prometheus.NewRegistry()
-	s := createTestAgentDB(t, reg, DefaultOptions())
+	opts := DefaultOptions()
+	opts.SetOutOfOrderTimeWindow(math.MaxInt64)
+	s := createTestAgentDB(t, reg, opts)
 	app := s.Appender(context.TODO())
 
 	// Let's add some samples in the [offset, offset+numDatapoints) range.
@@ -880,34 +883,58 @@ func TestDBAllowOOOSamples(t *testing.T) {
 }
 
 func TestDBRejectOOOSamples(t *testing.T) {
-	reg := prometheus.NewRegistry()
-	opts := DefaultOptions()
-	opts.RejectOOOSamples = true
-	s := createTestAgentDB(t, reg, opts)
-	app := s.Appender(context.TODO())
+	tc := []struct {
+		outOfOrderTimeWindow, firstTs, secondTs int64
+		reject                                  bool
+	}{
+		{0, 100, 101, false},
+		{0, 100, 100, true},
+		{0, 100, 99, true},
+		{100, 100, 1, false},
+		{100, 100, 0, true},
+	}
+
+	for _, c := range tc {
+		t.Run(fmt.Sprintf("outOfOrderTimeWindow=%d, firstTs=%d, secondTs=%d, reject=%t", c.outOfOrderTimeWindow, c.firstTs, c.secondTs, c.reject), func(t *testing.T) {
+			reg := prometheus.NewRegistry()
+			opts := DefaultOptions()
+			opts.SetOutOfOrderTimeWindow(c.outOfOrderTimeWindow)
+			s := createTestAgentDB(t, reg, opts)
+			app := s.Appender(context.TODO())
+
+			var expectedErr error
+			if c.reject {
+				expectedErr = storage.ErrOutOfOrderSample
+			}
 
-	lbls := labelsForTest(t.Name()+"_histogram", 1)
-	lset := labels.New(lbls[0]...)
-	_, err := app.AppendHistogram(0, lset, 1, tsdbutil.GenerateTestHistograms(1)[0], nil)
-	require.NoError(t, err)
-	err = app.Commit()
-	require.NoError(t, err)
-	_, err = app.AppendHistogram(0, lset, 0, tsdbutil.GenerateTestHistograms(1)[0], nil)
-	require.ErrorIs(t, err, storage.ErrOutOfOrderSample, "should reject OOO samples")
+			lbls := labelsForTest(t.Name()+"_histogram", 1)
+			lset := labels.New(lbls[0]...)
+			_, err := app.AppendHistogram(0, lset, c.firstTs, tsdbutil.GenerateTestHistograms(1)[0], nil)
+			require.NoError(t, err)
+			err = app.Commit()
+			require.NoError(t, err)
+			_, err = app.AppendHistogram(0, lset, c.secondTs, tsdbutil.GenerateTestHistograms(1)[0], nil)
+			require.ErrorIs(t, err, expectedErr)
 
-	lbls = labelsForTest(t.Name()+"_histogram", 1)
-	lset = labels.New(lbls[0]...)
-	_, err = app.Append(0, lset, 1, 0)
-	require.NoError(t, err)
-	err = app.Commit()
-	require.NoError(t, err)
-	_, err = app.Append(0, lset, 0, 0)
-	require.ErrorIs(t, err, storage.ErrOutOfOrderSample, "should reject OOO samples")
+			lbls = labelsForTest(t.Name(), 1)
+			lset = labels.New(lbls[0]...)
+			_, err = app.Append(0, lset, c.firstTs, 0)
+			require.NoError(t, err)
+			err = app.Commit()
+			require.NoError(t, err)
+			_, err = app.Append(0, lset, c.secondTs, 0)
+			require.ErrorIs(t, err, expectedErr)
 
-	m := gatherFamily(t, reg, "prometheus_agent_samples_appended_total")
-	require.Equal(t, float64(1), m.Metric[0].Counter.GetValue(), "agent wal mismatch of total appended samples")
-	require.Equal(t, float64(1), m.Metric[1].Counter.GetValue(), "agent wal mismatch of total appended histograms")
-	require.NoError(t, s.Close())
+			expectedAppendedSamples := float64(2)
+			if c.reject {
+				expectedAppendedSamples = 1
+			}
+			m := gatherFamily(t, reg, "prometheus_agent_samples_appended_total")
+			require.Equal(t, expectedAppendedSamples, m.Metric[0].Counter.GetValue(), "agent wal mismatch of total appended samples")
+			require.Equal(t, expectedAppendedSamples, m.Metric[1].Counter.GetValue(), "agent wal mismatch of total appended histograms")
+			require.NoError(t, s.Close())
+		})
+	}
 }
 
 func BenchmarkCreateSeries(b *testing.B) {