diff --git a/src/main/java/org/codehaus/plexus/archiver/AbstractUnArchiver.java b/src/main/java/org/codehaus/plexus/archiver/AbstractUnArchiver.java
index ab78577fa..2fa207240 100644
--- a/src/main/java/org/codehaus/plexus/archiver/AbstractUnArchiver.java
+++ b/src/main/java/org/codehaus/plexus/archiver/AbstractUnArchiver.java
@@ -401,16 +401,18 @@ else if ( isDirectory )
     protected boolean shouldExtractEntry( File targetDirectory, File targetFileName, String entryName, Date entryDate ) throws IOException
     {
         //     entryname  | entrydate | filename   | filedate | behavior
-        // (1) readme.txt | 1970      | readme.txt | 2020     | never overwrite
-        // (2) readme.txt | 2020      | readme.txt | 1970     | only overwrite when isOverWrite()
-        // (3) README.txt | 1970      | readme.txt | 2020     | case-insensitive filesystem: warn + never overwrite
+        // (1) readme.txt | 1970      | -          | -        | always extract if the file does not exist
+        // (2) readme.txt | 1970      | readme.txt | 2020     | do not overwrite unless isOverwrite() is true
+        // (3) readme.txt | 2020      | readme.txt | 1970     | always override when the file is older than the archive entry
+        // (4) README.txt | 1970      | readme.txt | 2020     | case-insensitive filesystem: warn + do not overwrite unless isOverwrite()
         //                                                      case-sensitive filesystem: extract without warning
-        // (4) README.txt | 2020      | readme.txt | 1970     | case-insensitive filesystem: warn + only overwrite when isOverWrite()
+        // (5) README.txt | 2020      | readme.txt | 1970     | case-insensitive filesystem: warn + overwrite because entry is newer
         //                                                      case-sensitive filesystem: extract without warning
 
         // The canonical file name follows the name of the archive entry, but takes into account the case-
         // sensitivity of the filesystem. So on a case-sensitive file system, file.exists() returns false for
-        // scenario (3) and (4).
+        // scenario (4) and (5).
+        // No matter the case sensitivity of the file system, file.exists() returns false when there is no file with the same name (1).
         if ( !targetFileName.exists() )
         {
             return true;
@@ -423,33 +425,20 @@ protected boolean shouldExtractEntry( File targetDirectory, File targetFileName,
                 targetDirectory.getCanonicalPath() + File.separatorChar,
                 "" )
                 + suffix;
-        boolean fileOnDiskIsNewerThanEntry = targetFileName.lastModified() >= entryDate.getTime();
+        boolean fileOnDiskIsOlderThanEntry = targetFileName.lastModified() < entryDate.getTime();
         boolean differentCasing = !entryName.equals( relativeCanonicalDestPath );
 
-        String casingMessage = String.format( Locale.ENGLISH, "Archive entry '%s' and existing file '%s' names differ only by case."
-                + " This may lead to an unexpected outcome on case-insensitive filesystems.", entryName, canonicalDestPath );
-
-        // (1)
-        if ( fileOnDiskIsNewerThanEntry )
-        {
-            // (3)
-            if ( differentCasing )
-            {
-                getLogger().warn( casingMessage );
-                casingMessageEmitted.incrementAndGet();
-            }
-            return false;
-        }
-
-        // (4)
+        // Warn for case (4) and (5) if the file system is case-insensitive
         if ( differentCasing )
         {
+            String casingMessage = String.format( Locale.ENGLISH, "Archive entry '%s' and existing file '%s' names differ only by case."
+                + " This may lead to an unexpected outcome on case-insensitive filesystems.", entryName, canonicalDestPath );
             getLogger().warn( casingMessage );
             casingMessageEmitted.incrementAndGet();
         }
 
-        // (2)
-        return isOverwrite();
+        // Override the existing file if isOverwrite() is true or if the file on disk is older than the one in the archive
+        return isOverwrite() || fileOnDiskIsOlderThanEntry;
     }
 
 }
diff --git a/src/test/java/org/codehaus/plexus/archiver/AbstractUnArchiverTest.java b/src/test/java/org/codehaus/plexus/archiver/AbstractUnArchiverTest.java
index 41b4fdebf..b5bfef2f1 100644
--- a/src/test/java/org/codehaus/plexus/archiver/AbstractUnArchiverTest.java
+++ b/src/test/java/org/codehaus/plexus/archiver/AbstractUnArchiverTest.java
@@ -91,11 +91,14 @@ public void shouldExtractWhenFileOnDiskDoesNotExist(  @TempDir File temporaryFol
         Date entryDate = new Date();
 
         // when & then
+        // always extract the file if it does not exist
+        assertTrue( abstractUnArchiver.shouldExtractEntry( temporaryFolder, file, entryname, entryDate ) );
+        abstractUnArchiver.setOverwrite( false );
         assertTrue( abstractUnArchiver.shouldExtractEntry( temporaryFolder, file, entryname, entryDate ) );
     }
 
     @Test
-    public void shouldNotExtractWhenFileOnDiskIsNewerThanEntryInArchive( @TempDir File temporaryFolder ) throws IOException
+    public void shouldExtractWhenFileOnDiskIsNewerThanEntryInArchive( @TempDir File temporaryFolder ) throws IOException
     {
         // given
         File file = new File( temporaryFolder, "whatever.txt" );
@@ -105,11 +108,14 @@ public void shouldNotExtractWhenFileOnDiskIsNewerThanEntryInArchive( @TempDir Fi
         Date entryDate = new Date( 0 );
 
         // when & then
+        // if the file is newer than archive entry, extract only if overwrite is true (default)
+        assertTrue( this.abstractUnArchiver.shouldExtractEntry( temporaryFolder, file, entryname, entryDate ) );
+        abstractUnArchiver.setOverwrite( false );
         assertFalse( this.abstractUnArchiver.shouldExtractEntry( temporaryFolder, file, entryname, entryDate ) );
     }
 
     @Test
-    public void shouldNotExtractWhenFileOnDiskIsNewerThanEntryInArchive_andWarnAboutDifferentCasing( @TempDir File temporaryFolder )
+    public void shouldExtractWhenFileOnDiskIsNewerThanEntryInArchive_andWarnAboutDifferentCasing( @TempDir File temporaryFolder )
         throws IOException
     {
         // given
@@ -120,7 +126,7 @@ public void shouldNotExtractWhenFileOnDiskIsNewerThanEntryInArchive_andWarnAbout
         Date entryDate = new Date( 0 );
 
         // when & then
-        assertFalse( this.abstractUnArchiver.shouldExtractEntry( temporaryFolder, file, entryname, entryDate ) );
+        assertTrue( this.abstractUnArchiver.shouldExtractEntry( temporaryFolder, file, entryname, entryDate ) );
         assertTrue( this.abstractUnArchiver.casingMessageEmitted.get() > 0 );
     }
 
@@ -135,12 +141,10 @@ public void shouldExtractWhenEntryInArchiveIsNewerThanFileOnDisk( @TempDir File
         Date entryDate = new Date( System.currentTimeMillis() );
 
         // when & then
-        this.abstractUnArchiver.setOverwrite( true );
+        // always extract the file if the archive entry is newer than the file on disk
         assertTrue( this.abstractUnArchiver.shouldExtractEntry( temporaryFolder, file, entryname, entryDate ) );
-
-        // when & then
         this.abstractUnArchiver.setOverwrite( false );
-        assertFalse( this.abstractUnArchiver.shouldExtractEntry( temporaryFolder, file, entryname, entryDate ) );
+        assertTrue( this.abstractUnArchiver.shouldExtractEntry( temporaryFolder, file, entryname, entryDate ) );
     }
 
     @Test
@@ -158,7 +162,7 @@ public void shouldExtractWhenEntryInArchiveIsNewerThanFileOnDiskAndWarnAboutDiff
         this.abstractUnArchiver.setOverwrite( true );
         assertTrue( this.abstractUnArchiver.shouldExtractEntry( temporaryFolder, file, entryname, entryDate ) );
         this.abstractUnArchiver.setOverwrite( false );
-        assertFalse( this.abstractUnArchiver.shouldExtractEntry( temporaryFolder, file, entryname, entryDate ) );
+        assertTrue( this.abstractUnArchiver.shouldExtractEntry( temporaryFolder, file, entryname, entryDate ) );
         assertTrue( this.abstractUnArchiver.casingMessageEmitted.get() > 0 );
     }