diff --git a/core/deployment/src/main/java/io/quarkus/deployment/pkg/steps/NativeImageBuildStep.java b/core/deployment/src/main/java/io/quarkus/deployment/pkg/steps/NativeImageBuildStep.java
index c2c122d68e01e..35cc15a7ba009 100644
--- a/core/deployment/src/main/java/io/quarkus/deployment/pkg/steps/NativeImageBuildStep.java
+++ b/core/deployment/src/main/java/io/quarkus/deployment/pkg/steps/NativeImageBuildStep.java
@@ -32,6 +32,7 @@
 import io.quarkus.deployment.pkg.builditem.NativeImageBuildItem;
 import io.quarkus.deployment.pkg.builditem.NativeImageSourceJarBuildItem;
 import io.quarkus.deployment.pkg.builditem.OutputTargetBuildItem;
+import io.quarkus.deployment.util.FileUtil;
 
 public class NativeImageBuildStep {
 
@@ -82,8 +83,12 @@ public NativeImageBuildItem build(NativeConfig nativeConfig, NativeImageSourceJa
             String containerRuntime = nativeConfig.containerRuntime.orElse("docker");
             // E.g. "/usr/bin/docker run -v {{PROJECT_DIR}}:/project --rm quarkus/graalvm-native-image"
             nativeImage = new ArrayList<>();
-            Collections.addAll(nativeImage, containerRuntime, "run", "-v",
-                    outputDir.toAbsolutePath() + ":/project:z");
+
+            String outputPath = outputDir.toAbsolutePath().toString();
+            if (IS_WINDOWS) {
+                outputPath = FileUtil.translateToVolumePath(outputPath);
+            }
+            Collections.addAll(nativeImage, containerRuntime, "run", "-v", outputPath + ":/project:z");
 
             if (IS_LINUX) {
                 if ("docker".equals(containerRuntime)) {
diff --git a/core/deployment/src/main/java/io/quarkus/deployment/util/FileUtil.java b/core/deployment/src/main/java/io/quarkus/deployment/util/FileUtil.java
index cafb22c254750..24607ced1447e 100644
--- a/core/deployment/src/main/java/io/quarkus/deployment/util/FileUtil.java
+++ b/core/deployment/src/main/java/io/quarkus/deployment/util/FileUtil.java
@@ -8,6 +8,9 @@
 import java.nio.file.Path;
 import java.nio.file.SimpleFileVisitor;
 import java.nio.file.attribute.BasicFileAttributes;
+import java.util.Optional;
+import java.util.regex.Matcher;
+import java.util.regex.Pattern;
 
 public class FileUtil {
 
@@ -48,4 +51,30 @@ public static byte[] readFileContents(InputStream inputStream) throws IOExceptio
         }
         return out.toByteArray();
     }
+
+    /**
+     * Translates a file path from the Windows Style to a syntax accepted by Docker,
+     * so that volumes be safely mounted in both Docker for Windows and the legacy
+     * Docker Toolbox.
+     * <p>
+     * <code>docker run -v //c/foo/bar:/somewhere (...)</code>
+     * <p>
+     * You should only use this method on Windows-style paths, and not Unix-style
+     * paths.
+     * 
+     * @see https://github.com/quarkusio/quarkus/issues/5360
+     * @param windowsStylePath A path formatted in Windows-style, e.g. "C:\foo\bar".
+     * @return A translated path accepted by Docker, e.g. "//c/foo/bar".
+     */
+    public static String translateToVolumePath(String windowsStylePath) {
+        String translated = windowsStylePath.replace('\\', '/');
+        Pattern p = Pattern.compile("^(\\w)(?:$|:(/)?(.*))");
+        Matcher m = p.matcher(translated);
+        if (m.matches()) {
+            String slash = Optional.ofNullable(m.group(2)).orElse("/");
+            String path = Optional.ofNullable(m.group(3)).orElse("");
+            return "//" + m.group(1).toLowerCase() + slash + path;
+        }
+        return translated;
+    }
 }
diff --git a/core/deployment/src/test/java/io/quarkus/deployment/util/FileUtilTest.java b/core/deployment/src/test/java/io/quarkus/deployment/util/FileUtilTest.java
new file mode 100644
index 0000000000000..dcc09761c4738
--- /dev/null
+++ b/core/deployment/src/test/java/io/quarkus/deployment/util/FileUtilTest.java
@@ -0,0 +1,28 @@
+package io.quarkus.deployment.util;
+
+import static io.quarkus.deployment.util.FileUtil.translateToVolumePath;
+import static org.junit.jupiter.api.Assertions.assertEquals;
+
+import org.junit.jupiter.api.Test;
+
+public class FileUtilTest {
+
+    @Test
+    public void testTranslateToVolumePath() {
+        // Windows-Style paths are formatted.
+        assertEquals("//c/", translateToVolumePath("C"));
+        assertEquals("//c/", translateToVolumePath("C:"));
+        assertEquals("//c/", translateToVolumePath("C:\\"));
+        assertEquals("//c/Users", translateToVolumePath("C:\\Users"));
+        assertEquals("//c/Users/Quarkus/lambdatest-1.0-SNAPSHOT-native-image-source-jar",
+                translateToVolumePath("C:\\Users\\Quarkus\\lambdatest-1.0-SNAPSHOT-native-image-source-jar"));
+
+        // Side effect for Unix-style path.
+        assertEquals("//c/Users/Quarkus", translateToVolumePath("c:/Users/Quarkus"));
+
+        // Side effects for fancy inputs - for the sake of documentation.
+        assertEquals("something/bizarre", translateToVolumePath("something\\bizarre"));
+        assertEquals("something.bizarre", translateToVolumePath("something.bizarre"));
+    }
+
+}