diff --git a/lib/events/dynamoevents/dynamoevents.go b/lib/events/dynamoevents/dynamoevents.go
index 7df2fa70e7316..6a958f6c5ca8b 100644
--- a/lib/events/dynamoevents/dynamoevents.go
+++ b/lib/events/dynamoevents/dynamoevents.go
@@ -1657,7 +1657,44 @@ func (l *eventsFetcher) processQueryOutput(output *dynamodb.QueryOutput) ([]even
 			l.checkpoint.EventKey = ""
 		}
 		// Stop early when the fetcher's total size exceeds the response size limit.
-		if l.totalSize+len(data) >= events.MaxEventBytesInResponse {
+		if l.totalSize+len(data) > events.MaxEventBytesInResponse {
+			// Encountered an event that would push the total page over the size limit.
+			// Return all processed events, and the next event will be picked up on the next page.
+			if len(out) > 0 {
+				if err := l.saveCheckpointAtEvent(out[len(out)-1]); err != nil {
+					return nil, false, trace.Wrap(err)
+				}
+				return out, true, nil
+			}
+
+			// A single event is larger than the max page size - the best we can
+			// do is try to trim it.
+			e.FieldsMap, err = trimToMaxSize(e.FieldsMap)
+			if err != nil {
+				return nil, false, trace.Wrap(err, "failed to trim event to max size")
+			}
+			trimmedData, err := json.Marshal(e.FieldsMap)
+			if err != nil {
+				return nil, false, trace.Wrap(err)
+			}
+
+			if l.totalSize+len(trimmedData) > events.MaxEventBytesInResponse {
+				// Failed to trim the event to size.
+				// Even if we fail to trim the event, we still try to return the oversized event.
+				l.log.WarnContext(context.Background(), "Failed to trim event exceeding maximum response size.",
+					"event_type", e.FieldsMap.GetType(),
+					"event_id", e.FieldsMap.GetID(),
+					"event_size", len(data),
+					"event_size_after_trim", len(trimmedData),
+				)
+			}
+			events.MetricQueriedTrimmedEvents.Inc()
+
+			l.totalSize += len(trimmedData)
+			out = append(out, e)
+			l.left--
+
+			// Since we reached the response size limit, simply return the event.
 			if err := l.saveCheckpointAtEvent(out[len(out)-1]); err != nil {
 				return nil, false, trace.Wrap(err)
 			}
@@ -1677,6 +1714,26 @@ func (l *eventsFetcher) processQueryOutput(output *dynamodb.QueryOutput) ([]even
 	return out, false, nil
 }
 
+// trimToMaxSize attempts to trim the event to fit into the maximum response size (MaxEventBytesInResponse).
+// If the event is larger than the maximum response size, it will be trimmed
+// to the maximum size, which may result in loss of data.
+// Trimming requires unmarshalling the event to apievents.AuditEvent and then
+// calling TrimToMaxSize on it.
+// This is not an efficient operation, but it is executed at most once per page,
+// and only when a single event exceeds the limit,
+// so it should not be a problem in practice.
+func trimToMaxSize(fields events.EventFields) (events.EventFields, error) {
+	event, err := events.FromEventFields(fields)
+	if err != nil {
+		return nil, trace.Wrap(err)
+	}
+
+	event = event.TrimToMaxSize(events.MaxEventBytesInResponse)
+
+	fields, err = events.ToEventFields(event)
+	return fields, trace.Wrap(err)
+}
+
 // saveCheckpointAtEvent updates the checkpoint iterator at the given event.
 // This overrides LastEvaluatedKey to resume future processing from this iterator.
 func (l *eventsFetcher) saveCheckpointAtEvent(e event) error {
diff --git a/lib/events/dynamoevents/dynamoevents_test.go b/lib/events/dynamoevents/dynamoevents_test.go
index c466fc448b41e..288bdbd3e2e8b 100644
--- a/lib/events/dynamoevents/dynamoevents_test.go
+++ b/lib/events/dynamoevents/dynamoevents_test.go
@@ -1028,11 +1028,32 @@ func Test_eventsFetcher_QueryByDateIndex(t *testing.T) {
 			AppName: "app-4",
 		},
 	}
+	bigUntrimmableEvent := &apievents.AppCreate{
+		Metadata: apievents.Metadata{
+			ID:   uuid.NewString(),
+			Time: time.Date(2025, 2, 5, 0, 0, 0, 0, time.UTC),
+			Type: events.AppCreateEvent,
+		},
+		AppMetadata: apievents.AppMetadata{
+			AppName: strings.Repeat("aaaaa", events.MaxEventBytesInResponse),
+		},
+	}
+	bigTrimmableEvent := &apievents.DatabaseSessionQuery{
+		Metadata: apievents.Metadata{
+			ID:   uuid.NewString(),
+			Time: time.Date(2025, 2, 5, 0, 0, 0, 0, time.UTC),
+			Type: events.DatabaseSessionQueryEvent,
+		},
+		DatabaseQuery: strings.Repeat("aaaaa", events.MaxEventBytesInResponse),
+	}
+	bigTrimmedEvent := bigTrimmableEvent.TrimToMaxSize(events.MaxEventBytesInResponse)
 
 	// have a deterministic session ID (UID) when used in test cases
 	key1 := eventToKey(event1)
 	key3 := eventToKey(event3)
 	key4 := eventToKey(event4)
+	keyUntrimmable := eventToKey(bigUntrimmableEvent)
+	keyTrimmed := eventToKey(bigTrimmedEvent)
 
 	tests := []struct {
 		name          string
@@ -1097,6 +1118,65 @@ func Test_eventsFetcher_QueryByDateIndex(t *testing.T) {
 			wantEvents: []apievents.AuditEvent{event1, event2, event3},
 			wantKey:    &key3,
 		},
+		{
+			name:  "events with big untrimmable event exceeding > MaxEventBytesInResponse",
+			limit: 10,
+			mockResponses: map[EventKey]mockResponse{
+				{}: {
+					events:    []apievents.AuditEvent{event1},
+					returnKey: &key1,
+				},
+				key1: {
+					events:    []apievents.AuditEvent{event2, event3, bigUntrimmableEvent},
+					returnKey: nil,
+				},
+			},
+			// we don't expect bigUntrimmableEvent because it should go to next batch
+			wantEvents: []apievents.AuditEvent{event1, event2, event3},
+			wantKey:    &key3,
+		},
+		{
+			name:  "only 1 big untrimmable event",
+			limit: 10,
+			mockResponses: map[EventKey]mockResponse{
+				{}: {
+					events:    []apievents.AuditEvent{bigUntrimmableEvent},
+					returnKey: nil,
+				},
+			},
+			// we still want to receive the untrimmable event
+			wantEvents: []apievents.AuditEvent{bigUntrimmableEvent},
+			wantKey:    &keyUntrimmable,
+		},
+		{
+			name:  "events with big trimmable event exceeding > MaxEventBytesInResponse",
+			limit: 10,
+			mockResponses: map[EventKey]mockResponse{
+				{}: {
+					events:    []apievents.AuditEvent{event1},
+					returnKey: &key1,
+				},
+				key1: {
+					events:    []apievents.AuditEvent{event2, event3, bigTrimmableEvent},
+					returnKey: nil,
+				},
+			},
+			// we don't expect bigTrimmableEvent because it should go to next batch
+			wantEvents: []apievents.AuditEvent{event1, event2, event3},
+			wantKey:    &key3,
+		},
+		{
+			name:  "only 1 big trimmable event",
+			limit: 10,
+			mockResponses: map[EventKey]mockResponse{
+				{}: {
+					events:    []apievents.AuditEvent{bigTrimmableEvent},
+					returnKey: nil,
+				},
+			},
+			wantEvents: []apievents.AuditEvent{bigTrimmedEvent},
+			wantKey:    &keyTrimmed,
+		},
 	}
 
 	for _, test := range tests {