diff --git a/src/main/java/org/asciidoctor/maven/AsciidoctorMojo.java b/src/main/java/org/asciidoctor/maven/AsciidoctorMojo.java
index 95782c7a..71e9f627 100644
--- a/src/main/java/org/asciidoctor/maven/AsciidoctorMojo.java
+++ b/src/main/java/org/asciidoctor/maven/AsciidoctorMojo.java
@@ -244,8 +244,9 @@ public void processSources(List<File> sourceFiles, ResourcesProcessor resourcesP
         final Set<File> uniquePaths = new HashSet<>();
         for (final File source : sourceFiles) {
             final File destinationPath = setDestinationPaths(source, optionsBuilder, sourceDir, this);
-            if (!uniquePaths.add(destinationPath))
+            if (!uniquePaths.add(destinationPath)) {
                 getLog().warn("Duplicated destination found: overwriting file: " + destinationPath.getAbsolutePath());
+            }
 
             convertFile(asciidoctor, optionsBuilder.asMap(), source);
 
@@ -379,9 +380,8 @@ public File setDestinationPaths(final File sourceFile, final OptionsBuilder opti
                 optionsBuilder.toDir(outputDir).destinationDir(outputDir);
             }
             final File outputFile = configuration.getOutputFile();
-            final String destinationDir = (String) optionsBuilder.asMap().get(Options.DESTINATION_DIR);
+            final String destinationDir = getDestinationDir(optionsBuilder);
             if (outputFile != null) {
-                // allow overriding the output file name
                 optionsBuilder.toFile(outputFile);
                 return outputFile.isAbsolute() ? outputFile : new File(destinationDir, outputFile.getPath());
             } else {
@@ -392,6 +392,12 @@ public File setDestinationPaths(final File sourceFile, final OptionsBuilder opti
         }
     }
 
+    private static String getDestinationDir(OptionsBuilder optionsBuilder) {
+        final Map<String, Object> options = optionsBuilder.asMap();
+        return (String) Optional.ofNullable(options.get(Options.DESTINATION_DIR))
+                .orElse(options.get(Options.TO_DIR));
+    }
+
     protected Asciidoctor getAsciidoctorInstance(String gemPath) throws MojoExecutionException {
         Asciidoctor asciidoctor = null;
         if (gemPath == null) {
diff --git a/src/test/java/org/asciidoctor/maven/AsciidoctorMojoTest.java b/src/test/java/org/asciidoctor/maven/AsciidoctorMojoTest.java
index d6342af5..31d840e7 100644
--- a/src/test/java/org/asciidoctor/maven/AsciidoctorMojoTest.java
+++ b/src/test/java/org/asciidoctor/maven/AsciidoctorMojoTest.java
@@ -5,12 +5,17 @@
 import org.apache.maven.model.Resource;
 import org.apache.maven.plugin.MojoExecutionException;
 import org.apache.maven.plugin.MojoFailureException;
+import org.asciidoctor.Options;
+import org.asciidoctor.OptionsBuilder;
 import org.asciidoctor.maven.extensions.ExtensionConfiguration;
 import org.asciidoctor.maven.io.AsciidoctorFileScanner;
 import org.asciidoctor.maven.io.ConsoleHolder;
 import org.asciidoctor.maven.test.processors.RequireCheckerTreeprocessor;
 import org.assertj.core.api.Assertions;
 import org.junit.jupiter.api.Test;
+import org.junit.jupiter.params.ParameterizedTest;
+import org.junit.jupiter.params.provider.NullAndEmptySource;
+import org.junit.jupiter.params.provider.ValueSource;
 
 import java.io.*;
 import java.nio.file.Files;
@@ -1069,4 +1074,22 @@ public void should_not_show_message_when_overwriting_files_using_outputFile_and_
         consoleHolder.release();
     }
 
+    @ParameterizedTest
+    @NullAndEmptySource
+    @ValueSource(strings = {"output.html"})
+    public void should_return_absolute_path_when_calculating_destination(String outputFile) throws MojoExecutionException {
+        // given
+        final AsciidoctorMojo mojo = mockAsciidoctorMojo();
+        mojo.setOutputDirectory(newOutputTestDirectory("overlapping-outputFile"));
+        if (outputFile != null) mojo.setOutputFile(outputFile);
+        final File source = new File("source.adoc");
+        final OptionsBuilder builder = Options.builder();
+        final File sourceDir = new File(".");
+
+        // when
+        File file = mojo.setDestinationPaths(source, builder, sourceDir, mojo);
+
+        // then
+        Assertions.assertThat(file).isAbsolute();
+    }
 }