diff --git a/src/main/java/io/reactivex/rxjava3/internal/operators/flowable/FlowableWindowTimed.java b/src/main/java/io/reactivex/rxjava3/internal/operators/flowable/FlowableWindowTimed.java
index d7c3e66e3d..0f1b43ae4a 100644
--- a/src/main/java/io/reactivex/rxjava3/internal/operators/flowable/FlowableWindowTimed.java
+++ b/src/main/java/io/reactivex/rxjava3/internal/operators/flowable/FlowableWindowTimed.java
@@ -498,7 +498,7 @@ void drainLoop() {
 
                     if (isHolder) {
                         ConsumerIndexHolder consumerIndexHolder = (ConsumerIndexHolder) o;
-                        if (restartTimerOnMaxSize || producerIndex == consumerIndexHolder.index) {
+                        if (!restartTimerOnMaxSize || producerIndex == consumerIndexHolder.index) {
                             w.onComplete();
                             count = 0;
                             w = UnicastProcessor.<T>create(bufferSize);
diff --git a/src/main/java/io/reactivex/rxjava3/internal/operators/observable/ObservableWindowTimed.java b/src/main/java/io/reactivex/rxjava3/internal/operators/observable/ObservableWindowTimed.java
index 58f94304ed..df10e149ba 100644
--- a/src/main/java/io/reactivex/rxjava3/internal/operators/observable/ObservableWindowTimed.java
+++ b/src/main/java/io/reactivex/rxjava3/internal/operators/observable/ObservableWindowTimed.java
@@ -444,7 +444,7 @@ void drainLoop() {
 
                     if (isHolder) {
                         ConsumerIndexHolder consumerIndexHolder = (ConsumerIndexHolder) o;
-                        if (restartTimerOnMaxSize || producerIndex == consumerIndexHolder.index) {
+                        if (!restartTimerOnMaxSize || producerIndex == consumerIndexHolder.index) {
                             w.onComplete();
                             count = 0;
                             w = UnicastSubject.create(bufferSize);
diff --git a/src/test/java/io/reactivex/rxjava3/flowable/FlowableWindowTests.java b/src/test/java/io/reactivex/rxjava3/flowable/FlowableWindowTests.java
index bcf3638316..d43b96f17f 100644
--- a/src/test/java/io/reactivex/rxjava3/flowable/FlowableWindowTests.java
+++ b/src/test/java/io/reactivex/rxjava3/flowable/FlowableWindowTests.java
@@ -16,11 +16,15 @@
 import static org.junit.Assert.*;
 
 import java.util.*;
+import java.util.concurrent.TimeUnit;
 
 import org.junit.Test;
 
 import io.reactivex.rxjava3.core.*;
 import io.reactivex.rxjava3.functions.*;
+import io.reactivex.rxjava3.processors.PublishProcessor;
+import io.reactivex.rxjava3.schedulers.TestScheduler;
+import io.reactivex.rxjava3.subscribers.TestSubscriber;
 
 public class FlowableWindowTests extends RxJavaTest {
 
@@ -50,4 +54,43 @@ public void accept(List<Integer> xs) {
         assertEquals(2, lists.size());
 
     }
+
+    @Test
+    public void timeSizeWindowAlternatingBounds() {
+        TestScheduler scheduler = new TestScheduler();
+        PublishProcessor<Integer> pp = PublishProcessor.create();
+
+        TestSubscriber<List<Integer>> ts = pp.window(5, TimeUnit.SECONDS, scheduler, 2)
+        .flatMapSingle(new Function<Flowable<Integer>, SingleSource<List<Integer>>>() {
+            @Override
+            public SingleSource<List<Integer>> apply(Flowable<Integer> v) throws Throwable {
+                return v.toList();
+            }
+        })
+        .test();
+
+        pp.onNext(1);
+        pp.onNext(2);
+        ts.assertValueCount(1); // size bound hit
+
+        scheduler.advanceTimeBy(1, TimeUnit.SECONDS);
+        pp.onNext(3);
+        scheduler.advanceTimeBy(6, TimeUnit.SECONDS);
+        ts.assertValueCount(2); // time bound hit
+
+        pp.onNext(4);
+        pp.onNext(5);
+
+        ts.assertValueCount(3); // size bound hit again
+
+        pp.onNext(4);
+
+        scheduler.advanceTimeBy(6, TimeUnit.SECONDS);
+
+        ts.assertValueCount(4)
+        .assertNoErrors()
+        .assertNotComplete();
+
+        ts.cancel();
+    }
 }
diff --git a/src/test/java/io/reactivex/rxjava3/internal/operators/flowable/FlowableWindowWithTimeTest.java b/src/test/java/io/reactivex/rxjava3/internal/operators/flowable/FlowableWindowWithTimeTest.java
index c357800827..7e055bd299 100644
--- a/src/test/java/io/reactivex/rxjava3/internal/operators/flowable/FlowableWindowWithTimeTest.java
+++ b/src/test/java/io/reactivex/rxjava3/internal/operators/flowable/FlowableWindowWithTimeTest.java
@@ -65,17 +65,19 @@ public void subscribe(Subscriber<? super String> subscriber) {
         Flowable<Flowable<String>> windowed = source.window(100, TimeUnit.MILLISECONDS, scheduler, 2);
         windowed.subscribe(observeWindow(list, lists));
 
-        scheduler.advanceTimeTo(100, TimeUnit.MILLISECONDS);
+        scheduler.advanceTimeTo(95, TimeUnit.MILLISECONDS);
         assertEquals(1, lists.size());
         assertEquals(lists.get(0), list("one", "two"));
 
-        scheduler.advanceTimeTo(200, TimeUnit.MILLISECONDS);
-        assertEquals(2, lists.size());
-        assertEquals(lists.get(1), list("three", "four"));
+        scheduler.advanceTimeTo(195, TimeUnit.MILLISECONDS);
+        assertEquals(3, lists.size());
+        assertTrue(lists.get(1).isEmpty());
+        assertEquals(lists.get(2), list("three", "four"));
 
         scheduler.advanceTimeTo(300, TimeUnit.MILLISECONDS);
-        assertEquals(3, lists.size());
-        assertEquals(lists.get(2), list("five"));
+        assertEquals(5, lists.size());
+        assertTrue(lists.get(3).isEmpty());
+        assertEquals(lists.get(4), list("five"));
     }
 
     @Test
diff --git a/src/test/java/io/reactivex/rxjava3/internal/operators/observable/ObservableWindowWithTimeTest.java b/src/test/java/io/reactivex/rxjava3/internal/operators/observable/ObservableWindowWithTimeTest.java
index ca9270448b..e56a094a8f 100644
--- a/src/test/java/io/reactivex/rxjava3/internal/operators/observable/ObservableWindowWithTimeTest.java
+++ b/src/test/java/io/reactivex/rxjava3/internal/operators/observable/ObservableWindowWithTimeTest.java
@@ -65,17 +65,19 @@ public void subscribe(Observer<? super String> observer) {
         Observable<Observable<String>> windowed = source.window(100, TimeUnit.MILLISECONDS, scheduler, 2);
         windowed.subscribe(observeWindow(list, lists));
 
-        scheduler.advanceTimeTo(100, TimeUnit.MILLISECONDS);
+        scheduler.advanceTimeTo(95, TimeUnit.MILLISECONDS);
         assertEquals(1, lists.size());
         assertEquals(lists.get(0), list("one", "two"));
 
-        scheduler.advanceTimeTo(200, TimeUnit.MILLISECONDS);
-        assertEquals(2, lists.size());
-        assertEquals(lists.get(1), list("three", "four"));
+        scheduler.advanceTimeTo(195, TimeUnit.MILLISECONDS);
+        assertEquals(3, lists.size());
+        assertTrue(lists.get(1).isEmpty());
+        assertEquals(lists.get(2), list("three", "four"));
 
         scheduler.advanceTimeTo(300, TimeUnit.MILLISECONDS);
-        assertEquals(3, lists.size());
-        assertEquals(lists.get(2), list("five"));
+        assertEquals(5, lists.size());
+        assertTrue(lists.get(3).isEmpty());
+        assertEquals(lists.get(4), list("five"));
     }
 
     @Test
diff --git a/src/test/java/io/reactivex/rxjava3/observable/ObservableWindowTests.java b/src/test/java/io/reactivex/rxjava3/observable/ObservableWindowTests.java
index bfdeed1c6d..1d4a62f7f3 100644
--- a/src/test/java/io/reactivex/rxjava3/observable/ObservableWindowTests.java
+++ b/src/test/java/io/reactivex/rxjava3/observable/ObservableWindowTests.java
@@ -16,12 +16,16 @@
 import static org.junit.Assert.*;
 
 import java.util.*;
+import java.util.concurrent.TimeUnit;
 
 import org.junit.Test;
 
+import io.reactivex.rxjava3.core.*;
 import io.reactivex.rxjava3.core.Observable;
-import io.reactivex.rxjava3.core.RxJavaTest;
 import io.reactivex.rxjava3.functions.*;
+import io.reactivex.rxjava3.observers.TestObserver;
+import io.reactivex.rxjava3.schedulers.*;
+import io.reactivex.rxjava3.subjects.PublishSubject;
 
 public class ObservableWindowTests extends RxJavaTest {
 
@@ -51,4 +55,43 @@ public void accept(List<Integer> xs) {
         assertEquals(2, lists.size());
 
     }
+
+    @Test
+    public void timeSizeWindowAlternatingBounds() {
+        TestScheduler scheduler = new TestScheduler();
+        PublishSubject<Integer> ps = PublishSubject.create();
+
+        TestObserver<List<Integer>> to = ps.window(5, TimeUnit.SECONDS, scheduler, 2)
+        .flatMapSingle(new Function<Observable<Integer>, SingleSource<List<Integer>>>() {
+            @Override
+            public SingleSource<List<Integer>> apply(Observable<Integer> v) throws Throwable {
+                return v.toList();
+            }
+        })
+        .test();
+
+        ps.onNext(1);
+        ps.onNext(2);
+        to.assertValueCount(1); // size bound hit
+
+        scheduler.advanceTimeBy(1, TimeUnit.SECONDS);
+        ps.onNext(3);
+        scheduler.advanceTimeBy(6, TimeUnit.SECONDS);
+        to.assertValueCount(2); // time bound hit
+
+        ps.onNext(4);
+        ps.onNext(5);
+
+        to.assertValueCount(3); // size bound hit again
+
+        ps.onNext(4);
+
+        scheduler.advanceTimeBy(6, TimeUnit.SECONDS);
+
+        to.assertValueCount(4)
+        .assertNoErrors()
+        .assertNotComplete();
+
+        to.dispose();
+    }
 }