diff --git a/x-pack/plugin/watcher/src/main/java/org/elasticsearch/xpack/watcher/trigger/schedule/CronnableSchedule.java b/x-pack/plugin/watcher/src/main/java/org/elasticsearch/xpack/watcher/trigger/schedule/CronnableSchedule.java
index ec309c69476cc..695c9b192eaa6 100644
--- a/x-pack/plugin/watcher/src/main/java/org/elasticsearch/xpack/watcher/trigger/schedule/CronnableSchedule.java
+++ b/x-pack/plugin/watcher/src/main/java/org/elasticsearch/xpack/watcher/trigger/schedule/CronnableSchedule.java
@@ -13,20 +13,15 @@
 
 public abstract class CronnableSchedule implements Schedule {
 
-    private static final Comparator<Cron> CRON_COMPARATOR = new Comparator<Cron>() {
-        @Override
-        public int compare(Cron c1, Cron c2) {
-            return c1.expression().compareTo(c2.expression());
-        }
-    };
+    private static final Comparator<Cron> CRON_COMPARATOR = Comparator.comparing(Cron::expression);
 
     protected final Cron[] crons;
 
-    public CronnableSchedule(String... expressions) {
+    CronnableSchedule(String... expressions) {
         this(crons(expressions));
     }
 
-    public CronnableSchedule(Cron... crons) {
+    private CronnableSchedule(Cron... crons) {
         assert crons.length > 0;
         this.crons = crons;
         Arrays.sort(crons, CRON_COMPARATOR);
@@ -37,7 +32,15 @@ public long nextScheduledTimeAfter(long startTime, long time) {
         assert time >= startTime;
         long nextTime = Long.MAX_VALUE;
         for (Cron cron : crons) {
-            nextTime = Math.min(nextTime, cron.getNextValidTimeAfter(time));
+            long nextValidTimeAfter = cron.getNextValidTimeAfter(time);
+
+            boolean previousCronExpired = nextTime == -1;
+            boolean currentCronValid = nextValidTimeAfter > -1;
+            if (previousCronExpired && currentCronValid) {
+                nextTime = nextValidTimeAfter;
+            } else {
+                nextTime = Math.min(nextTime, nextValidTimeAfter);
+            }
         }
         return nextTime;
     }
diff --git a/x-pack/plugin/watcher/src/test/java/org/elasticsearch/xpack/watcher/trigger/schedule/CronScheduleTests.java b/x-pack/plugin/watcher/src/test/java/org/elasticsearch/xpack/watcher/trigger/schedule/CronScheduleTests.java
index 1ade767410b53..6cbdf6e122656 100644
--- a/x-pack/plugin/watcher/src/test/java/org/elasticsearch/xpack/watcher/trigger/schedule/CronScheduleTests.java
+++ b/x-pack/plugin/watcher/src/test/java/org/elasticsearch/xpack/watcher/trigger/schedule/CronScheduleTests.java
@@ -11,11 +11,15 @@
 import org.elasticsearch.common.xcontent.XContentParser;
 import org.elasticsearch.common.xcontent.json.JsonXContent;
 
+import java.time.ZoneOffset;
+import java.time.ZonedDateTime;
+
 import static org.elasticsearch.common.xcontent.XContentFactory.jsonBuilder;
 import static org.hamcrest.Matchers.arrayWithSize;
 import static org.hamcrest.Matchers.hasItemInArray;
 import static org.hamcrest.Matchers.instanceOf;
 import static org.hamcrest.Matchers.is;
+import static org.hamcrest.Matchers.not;
 
 public class CronScheduleTests extends ScheduleTestCase {
     public void testInvalid() throws Exception {
@@ -54,18 +58,25 @@ public void testParseMultiple() throws Exception {
         assertThat(crons, hasItemInArray("0 0/3 * * * ?"));
     }
 
+    public void testMultipleCronsNextScheduledAfter() {
+        CronSchedule schedule = new CronSchedule("0 5 9 1 1 ? 2019", "0 5 9 1 1 ? 2020", "0 5 9 1 1 ? 2017");
+        ZonedDateTime start2019 = ZonedDateTime.of(2019, 1, 1, 0, 0, 0, 0, ZoneOffset.UTC);
+        ZonedDateTime start2020 = ZonedDateTime.of(2020, 1, 1, 0, 0, 0, 0, ZoneOffset.UTC);
+        long firstSchedule = schedule.nextScheduledTimeAfter(0, start2019.toInstant().toEpochMilli());
+        long secondSchedule = schedule.nextScheduledTimeAfter(0, start2020.toInstant().toEpochMilli());
+
+        assertThat(firstSchedule, is(not(-1L)));
+        assertThat(secondSchedule, is(not(-1L)));
+        assertThat(firstSchedule, is(not(secondSchedule)));
+    }
+
     public void testParseInvalidBadExpression() throws Exception {
         XContentBuilder builder = jsonBuilder().value("0 0/5 * * ?");
         BytesReference bytes = BytesReference.bytes(builder);
         XContentParser parser = createParser(JsonXContent.jsonXContent, bytes);
         parser.nextToken();
-        try {
-            new CronSchedule.Parser().parse(parser);
-            fail("expected cron parsing to fail when using invalid cron expression");
-        } catch (ElasticsearchParseException pe) {
-            // expected
-            assertThat(pe.getCause(), instanceOf(IllegalArgumentException.class));
-        }
+        ElasticsearchParseException e = expectThrows(ElasticsearchParseException.class, () -> new CronSchedule.Parser().parse(parser));
+        assertThat(e.getCause(), instanceOf(IllegalArgumentException.class));
     }
 
     public void testParseInvalidEmpty() throws Exception {