diff --git a/lib/events/dynamoevents/dynamoevents.go b/lib/events/dynamoevents/dynamoevents.go
index 701ea5536602f..f2490d6e0464a 100644
--- a/lib/events/dynamoevents/dynamoevents.go
+++ b/lib/events/dynamoevents/dynamoevents.go
@@ -642,6 +642,17 @@ func (l *Log) searchEventsRaw(ctx context.Context, fromUTC, toUTC time.Time, nam
 		return nil, "", trace.Wrap(err)
 	}
 
+	if checkpoint.Date != "" {
+		if t, err := time.Parse(time.DateOnly, checkpoint.Date); err == nil {
+			d := fromUTC.Unix()
+			// if fromUTC at 00:00:00 is bigger than the cursor,
+			// reset the cursor and advance to next day.
+			if time.Unix(d-d%(24*3600), 0).After(t) {
+				checkpoint = checkpointKey{}
+			}
+		}
+	}
+
 	totalSize := 0
 	dates := daysBetween(fromUTC, toUTC)
 	if order == types.EventOrderDescending {
@@ -662,9 +673,15 @@ func (l *Log) searchEventsRaw(ctx context.Context, fromUTC, toUTC time.Time, nam
 	// We need to perform a guard check on the length of `dates` here in case a query is submitted with
 	// `toUTC` occurring before `fromUTC`.
 	if checkpoint.Date != "" && len(dates) > 0 {
-		for dates[0] != checkpoint.Date {
+		for len(dates) > 0 && dates[0] != checkpoint.Date {
 			dates = dates[1:]
 		}
+		// if the initial data wasn't found in [fromUTC,toUTC]
+		// dates will be empty and we can return early since we
+		// won't find any events.
+		if len(dates) == 0 {
+			return nil, "", nil
+		}
 	}
 
 	foundStart := checkpoint.EventKey == ""
diff --git a/lib/events/dynamoevents/dynamoevents_test.go b/lib/events/dynamoevents/dynamoevents_test.go
index 4d77a1f4a1b47..54004a0f148f1 100644
--- a/lib/events/dynamoevents/dynamoevents_test.go
+++ b/lib/events/dynamoevents/dynamoevents_test.go
@@ -18,6 +18,7 @@ package dynamoevents
 
 import (
 	"context"
+	"encoding/json"
 	"fmt"
 	"math/rand"
 	"net/url"
@@ -114,6 +115,32 @@ func TestSearchSessionEvensBySessionID(t *testing.T) {
 	tt.suite.SearchSessionEventsBySessionID(t)
 }
 
+// TestCheckpointOutsideOfWindow tests if [Log] doesn't panic
+// if checkpoint date is outside of the window [fromUTC,toUTC].
+func TestCheckpointOutsideOfWindow(t *testing.T) {
+	tt := &Log{}
+
+	key := checkpointKey{
+		Date: "2022-10-02",
+	}
+	keyB, err := json.Marshal(key)
+	require.NoError(t, err)
+
+	results, nextKey, err := tt.SearchEvents(
+		context.Background(),
+		events.SearchEventsRequest{
+			From:     time.Date(2021, 10, 10, 0, 0, 0, 0, time.UTC),
+			To:       time.Date(2021, 11, 10, 0, 0, 0, 0, time.UTC),
+			Limit:    100,
+			StartKey: string(keyB),
+			Order:    types.EventOrderAscending,
+		},
+	)
+	require.NoError(t, err)
+	require.Empty(t, results)
+	require.Empty(t, nextKey)
+}
+
 func TestSizeBreak(t *testing.T) {
 	tt := setupDynamoContext(t)