diff --git a/core/src/main/java/hudson/tasks/ArtifactArchiver.java b/core/src/main/java/hudson/tasks/ArtifactArchiver.java
index 02137ad369464..edfa7eeb2964d 100644
--- a/core/src/main/java/hudson/tasks/ArtifactArchiver.java
+++ b/core/src/main/java/hudson/tasks/ArtifactArchiver.java
@@ -389,7 +389,9 @@ public boolean isApplicable(Class<? extends AbstractProject> jobType) {
                             if (bd instanceof LogRotator) {
                                 LogRotator lr = (LogRotator) bd;
                                 if (lr.getArtifactNumToKeep() == -1) {
-                                    p.setBuildDiscarder(new LogRotator(lr.getDaysToKeep(), lr.getNumToKeep(), lr.getArtifactDaysToKeep(), 1));
+                                    LogRotator newLr = new LogRotator(lr.getDaysToKeep(), lr.getNumToKeep(), lr.getArtifactDaysToKeep(), 1);
+                                    newLr.setRemoveLastSuccessfulBuild(lr.isRemoveLastSuccessfulBuild());
+                                    p.setBuildDiscarder(newLr);
                                 } else {
                                     LOG.log(Level.WARNING, "will not clobber artifactNumToKeep={0} in {1}", new Object[] {lr.getArtifactNumToKeep(), p});
                                 }
diff --git a/core/src/main/java/hudson/tasks/LogRotator.java b/core/src/main/java/hudson/tasks/LogRotator.java
index 3d5f3975808a6..901429c95b4fb 100644
--- a/core/src/main/java/hudson/tasks/LogRotator.java
+++ b/core/src/main/java/hudson/tasks/LogRotator.java
@@ -50,6 +50,7 @@
 import jenkins.util.io.CompositeIOException;
 import org.jenkinsci.Symbol;
 import org.kohsuke.stapler.DataBoundConstructor;
+import org.kohsuke.stapler.DataBoundSetter;
 
 /**
  * Default implementation of {@link BuildDiscarder}.
@@ -108,6 +109,12 @@ public CollatedLogRotatorException(String msg, Collection<Exception> values) {
      */
     private final Integer artifactNumToKeep;
 
+    /**
+     * If enabled also remove last successful build.
+     * @since 2.464
+     */
+    private boolean removeLastSuccessfulBuild;
+
     @DataBoundConstructor
     public LogRotator(String daysToKeepStr, String numToKeepStr, String artifactDaysToKeepStr, String artifactNumToKeepStr) {
         this (parse(daysToKeepStr), parse(numToKeepStr),
@@ -140,6 +147,11 @@ public LogRotator(int daysToKeep, int numToKeep, int artifactDaysToKeep, int art
 
     }
 
+    @DataBoundSetter
+    public void setRemoveLastSuccessfulBuild(boolean removeLastSuccessfulBuild) {
+        this.removeLastSuccessfulBuild = removeLastSuccessfulBuild;
+    }
+
     @Override
     @SuppressWarnings("rawtypes")
     public void perform(Job<?, ?> job) throws IOException, InterruptedException {
@@ -148,9 +160,9 @@ public void perform(Job<?, ?> job) throws IOException, InterruptedException {
 
         LOGGER.log(FINE, "Running the log rotation for {0} with numToKeep={1} daysToKeep={2} artifactNumToKeep={3} artifactDaysToKeep={4}", new Object[] {job, numToKeep, daysToKeep, artifactNumToKeep, artifactDaysToKeep});
 
-        // always keep the last successful and the last stable builds
-        Run lsb = job.getLastSuccessfulBuild();
-        Run lstb = job.getLastStableBuild();
+        // if configured keep the last successful and the last stable builds
+        Run lsb = removeLastSuccessfulBuild ? null : job.getLastSuccessfulBuild();
+        Run lstb = removeLastSuccessfulBuild ? null : job.getLastStableBuild();
 
         if (numToKeep != -1) {
             // Note that RunList.size is deprecated, and indeed here we are loading all the builds of the job.
@@ -270,6 +282,10 @@ public int getArtifactNumToKeep() {
         return unbox(artifactNumToKeep);
     }
 
+    public boolean isRemoveLastSuccessfulBuild() {
+        return removeLastSuccessfulBuild;
+    }
+
     public String getDaysToKeepStr() {
         return toString(daysToKeep);
     }
diff --git a/core/src/main/resources/hudson/tasks/LogRotator/config.jelly b/core/src/main/resources/hudson/tasks/LogRotator/config.jelly
index b071ec3b9108e..c62ea6dfefca7 100644
--- a/core/src/main/resources/hudson/tasks/LogRotator/config.jelly
+++ b/core/src/main/resources/hudson/tasks/LogRotator/config.jelly
@@ -41,5 +41,9 @@ THE SOFTWARE.
              description="${%if not empty, only up to this number of builds have their artifacts retained}" field="artifactNumToKeepStr">
       <f:number clazz="positive-number" min="1" step="1" />
     </f:entry>
+    <f:entry title="${%Remove last stable and successful builds}"
+             field="removeLastSuccessfulBuild">
+      <f:booleanRadio />
+    </f:entry>
   </f:advanced>
 </j:jelly>
diff --git a/test/src/test/java/hudson/tasks/LogRotatorTest.java b/test/src/test/java/hudson/tasks/LogRotatorTest.java
index 8a408b758b01b..05c3b854bf243 100644
--- a/test/src/test/java/hudson/tasks/LogRotatorTest.java
+++ b/test/src/test/java/hudson/tasks/LogRotatorTest.java
@@ -68,7 +68,7 @@ public class LogRotatorTest {
     @Test
     public void successVsFailure() throws Exception {
         FreeStyleProject project = j.createFreeStyleProject();
-        project.setLogRotator(new LogRotator(-1, 2, -1, -1));
+        project.setBuildDiscarder(new LogRotator(-1, 2, -1, -1));
         j.buildAndAssertSuccess(project); // #1
         project.getBuildersList().replaceBy(Set.of(new FailureBuilder()));
         j.buildAndAssertStatus(Result.FAILURE, project); // #2
@@ -82,11 +82,25 @@ public void successVsFailure() throws Exception {
         assertEquals(3, numberOf(project.getLastFailedBuild()));
     }
 
+    @Test
+    public void successVsFailureWithRemoveLastSuccess() throws Exception {
+        FreeStyleProject project = j.createFreeStyleProject();
+        LogRotator logRotator = new LogRotator(-1, 1, -1, -1);
+        logRotator.setRemoveLastSuccessfulBuild(true);
+        project.setBuildDiscarder(logRotator);
+        project.getPublishersList().replaceBy(Set.of(new TestsFail()));
+        j.buildAndAssertStatus(Result.UNSTABLE, project); // #1
+        project.getBuildersList().replaceBy(Set.of(new FailureBuilder()));
+        j.buildAndAssertStatus(Result.FAILURE, project); // #2
+        assertNull(project.getBuildByNumber(1));
+        assertEquals(2, numberOf(project.getLastFailedBuild()));
+    }
+
     @Test
     @Issue("JENKINS-2417")
     public void stableVsUnstable() throws Exception {
         FreeStyleProject project = j.createFreeStyleProject();
-        project.setLogRotator(new LogRotator(-1, 2, -1, -1));
+        project.setBuildDiscarder(new LogRotator(-1, 2, -1, -1));
         j.buildAndAssertSuccess(project); // #1
         project.getPublishersList().replaceBy(Set.of(new TestsFail()));
         j.buildAndAssertStatus(Result.UNSTABLE, project); // #2
@@ -98,11 +112,28 @@ public void stableVsUnstable() throws Exception {
         assertNull(project.getBuildByNumber(2));
     }
 
+    @Test
+    public void stableVsUnstableWithRemoveLastStable() throws Exception {
+        FreeStyleProject project = j.createFreeStyleProject();
+        LogRotator logRotator = new LogRotator(-1, 1, -1, -1);
+        logRotator.setRemoveLastSuccessfulBuild(true);
+        project.setBuildDiscarder(logRotator);
+        j.buildAndAssertSuccess(project); // #1
+        project.getPublishersList().replaceBy(Set.of(new TestsFail()));
+        j.buildAndAssertStatus(Result.UNSTABLE, project); // #2
+        project.getBuildersList().replaceBy(Set.of(new FailureBuilder()));
+        j.buildAndAssertStatus(Result.FAILURE, project); // #3
+        assertNull(project.getBuildByNumber(1));
+        assertNull(project.getBuildByNumber(2));
+        assertEquals(-1, numberOf(project.getLastSuccessfulBuild()));
+        assertEquals(3, numberOf(project.getLastBuild()));
+    }
+
     @Test
     @Issue("JENKINS-834")
     public void artifactDelete() throws Exception {
         FreeStyleProject project = j.createFreeStyleProject();
-        project.setLogRotator(new LogRotator(-1, 6, -1, 2));
+        project.setBuildDiscarder(new LogRotator(-1, 6, -1, 2));
         project.getPublishersList().replaceBy(Set.of(new ArtifactArchiver("f", "", true, false)));
         j.buildAndAssertStatus(Result.FAILURE, project); // #1
         assertFalse(project.getBuildByNumber(1).getHasArtifacts());