diff --git a/CronTriggeringPolicy.java b/CronTriggeringPolicy_patched.java
index 6b8af2a..f9bd1c0 100644
--- a/CronTriggeringPolicy.java
+++ b/CronTriggeringPolicy_patched.java
@@ -16,8 +16,11 @@
  */
 package org.apache.logging.log4j.core.appender.rolling;
 
+import static com.cronutils.model.CronType.QUARTZ;
+
 import java.text.ParseException;
-import java.util.Calendar;
+import java.time.Instant;
+import java.time.ZoneId;
 import java.util.Date;
 import java.util.concurrent.TimeUnit;
 
@@ -31,6 +34,10 @@ import org.apache.logging.log4j.core.config.plugins.PluginConfiguration;
 import org.apache.logging.log4j.core.config.plugins.PluginFactory;
 import org.apache.logging.log4j.core.util.CronExpression;
 
+import com.cronutils.model.definition.CronDefinitionBuilder;
+import com.cronutils.model.time.ExecutionTime;
+import com.cronutils.parser.CronParser;
+
 /**
  * Rolls a file over based on a cron schedule.
  */
@@ -43,7 +50,7 @@ public final class CronTriggeringPolicy extends AbstractTriggeringPolicy {
     private final CronExpression cronExpression;
     private final Configuration configuration;
     private final boolean checkOnStartup;
-    private volatile Date nextRollDate;
+    private volatile Date lastRollDate;
     private CronScheduledFuture<?> future;
 
     private CronTriggeringPolicy(final CronExpression schedule, final boolean checkOnStartup,
@@ -62,14 +69,22 @@ public final class CronTriggeringPolicy extends AbstractTriggeringPolicy {
     @Override
     public void initialize(final RollingFileManager aManager) {
         this.manager = aManager;
-        final Date nextDate = new Date(this.manager.getFileTime());
-        nextRollDate = cronExpression.getNextValidTimeAfter(nextDate);
-        if (checkOnStartup) {
-            if (nextRollDate.getTime() < System.currentTimeMillis()) {
-                rollover();
-            }
+
+        final Date now = new Date();
+        final ExecutionTime executionTime = ExecutionTime.forCron(
+            new CronParser(CronDefinitionBuilder.instanceDefinitionFor(QUARTZ)).parse(cronExpression.getCronExpression()));
+        final Instant lastRollForFile =
+            executionTime.lastExecution(new Date(manager.getFileTime()).toInstant().atZone(ZoneId.systemDefault())).toInstant();
+        final Instant lastRegularRoll =
+            executionTime.lastExecution(now.toInstant().atZone(ZoneId.systemDefault())).toInstant();
+
+        if (checkOnStartup && lastRollForFile.isBefore(lastRegularRoll)) {
+            lastRollDate = Date.from(lastRollForFile);
+            rollover();
         }
-        future = configuration.getScheduler().scheduleWithCron(cronExpression, new CronTrigger());
+
+        lastRollDate = Date.from(lastRegularRoll);
+        future = configuration.getScheduler().scheduleWithCron(cronExpression, now, new CronTrigger());
     }
 
     /**
@@ -128,13 +143,12 @@ public final class CronTriggeringPolicy extends AbstractTriggeringPolicy {
     }
 
     private void rollover() {
-        manager.getPatternProcessor().setPrevFileTime(nextRollDate.getTime());
+        manager.getPatternProcessor().setPrevFileTime(lastRollDate.getTime());
         manager.rollover();
-        final Date fireDate = future.getFireTime();
-        final Calendar cal = Calendar.getInstance();
-        cal.setTime(fireDate);
-        cal.add(Calendar.SECOND, -1);
-        nextRollDate = cal.getTime();
+        if (future != null)
+        {
+            lastRollDate = future.getFireTime();
+        }
     }
 
     @Override