diff --git a/core/deployment/src/main/java/io/quarkus/deployment/pkg/steps/NativeImageBuildLocalContainerRunner.java b/core/deployment/src/main/java/io/quarkus/deployment/pkg/steps/NativeImageBuildLocalContainerRunner.java
index da449581e169e..8cabc251e4a3b 100644
--- a/core/deployment/src/main/java/io/quarkus/deployment/pkg/steps/NativeImageBuildLocalContainerRunner.java
+++ b/core/deployment/src/main/java/io/quarkus/deployment/pkg/steps/NativeImageBuildLocalContainerRunner.java
@@ -40,7 +40,8 @@ protected List<String> getContainerRuntimeBuildArgs() {
         List<String> containerRuntimeArgs = super.getContainerRuntimeBuildArgs();
         String volumeOutputPath = outputPath;
         if (SystemUtils.IS_OS_WINDOWS) {
-            volumeOutputPath = FileUtil.translateToVolumePath(volumeOutputPath);
+            volumeOutputPath = FileUtil.translateToVolumePath(volumeOutputPath,
+                    containerRuntime == ContainerRuntimeUtil.ContainerRuntime.PODMAN);
         }
 
         Collections.addAll(containerRuntimeArgs, "-v",
diff --git a/core/deployment/src/main/java/io/quarkus/deployment/pkg/steps/UpxCompressionBuildStep.java b/core/deployment/src/main/java/io/quarkus/deployment/pkg/steps/UpxCompressionBuildStep.java
index 043ff6fd1e38c..a1023f7fd4448 100644
--- a/core/deployment/src/main/java/io/quarkus/deployment/pkg/steps/UpxCompressionBuildStep.java
+++ b/core/deployment/src/main/java/io/quarkus/deployment/pkg/steps/UpxCompressionBuildStep.java
@@ -122,7 +122,8 @@ private boolean runUpxInContainer(NativeImageBuildItem nativeImage, NativeConfig
 
         String volumeOutputPath = nativeImage.getPath().toFile().getParentFile().getAbsolutePath();
         if (SystemUtils.IS_OS_WINDOWS) {
-            volumeOutputPath = FileUtil.translateToVolumePath(volumeOutputPath);
+            volumeOutputPath = FileUtil.translateToVolumePath(volumeOutputPath,
+                    containerRuntime == ContainerRuntimeUtil.ContainerRuntime.PODMAN);
         } else if (SystemUtils.IS_OS_LINUX) {
             String uid = getLinuxID("-ur");
             String gid = getLinuxID("-gr");
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 711072d50b166..de20b26d2f03f 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
@@ -78,14 +78,15 @@ public static byte[] readFileContents(InputStream inputStream) throws IOExceptio
      * @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) {
+    public static String translateToVolumePath(String windowsStylePath, boolean isPodman) {
         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;
+            // Ad `/' and `//' see https://github.com/containers/podman/issues/14414
+            return (isPodman ? "/" : "//") + 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
index dcc09761c4738..97733a37bde7f 100644
--- a/core/deployment/src/test/java/io/quarkus/deployment/util/FileUtilTest.java
+++ b/core/deployment/src/test/java/io/quarkus/deployment/util/FileUtilTest.java
@@ -10,19 +10,20 @@ 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/tmp/code-with-quarkus", translateToVolumePath("C:\\tmp\\code-with-quarkus", true));
+        assertEquals("//c/", translateToVolumePath("C", false));
+        assertEquals("//c/", translateToVolumePath("C:", false));
+        assertEquals("//c/", translateToVolumePath("C:\\", false));
+        assertEquals("//c/Users", translateToVolumePath("C:\\Users", false));
         assertEquals("//c/Users/Quarkus/lambdatest-1.0-SNAPSHOT-native-image-source-jar",
-                translateToVolumePath("C:\\Users\\Quarkus\\lambdatest-1.0-SNAPSHOT-native-image-source-jar"));
+                translateToVolumePath("C:\\Users\\Quarkus\\lambdatest-1.0-SNAPSHOT-native-image-source-jar", false));
 
         // Side effect for Unix-style path.
-        assertEquals("//c/Users/Quarkus", translateToVolumePath("c:/Users/Quarkus"));
+        assertEquals("//c/Users/Quarkus", translateToVolumePath("c:/Users/Quarkus", false));
 
         // Side effects for fancy inputs - for the sake of documentation.
-        assertEquals("something/bizarre", translateToVolumePath("something\\bizarre"));
-        assertEquals("something.bizarre", translateToVolumePath("something.bizarre"));
+        assertEquals("something/bizarre", translateToVolumePath("something\\bizarre", false));
+        assertEquals("something.bizarre", translateToVolumePath("something.bizarre", false));
     }
 
 }