diff --git a/test/jdk/tools/jpackage/helpers/jdk/jpackage/test/FileAssociations.java b/test/jdk/tools/jpackage/helpers/jdk/jpackage/test/FileAssociations.java
index ceb0dedcb6fa8..b3527e0b4ff33 100644
--- a/test/jdk/tools/jpackage/helpers/jdk/jpackage/test/FileAssociations.java
+++ b/test/jdk/tools/jpackage/helpers/jdk/jpackage/test/FileAssociations.java
@@ -22,9 +22,16 @@
  */
 package jdk.jpackage.test;
 
+import java.awt.Desktop;
+import java.io.IOException;
 import java.nio.file.Path;
+import java.util.ArrayList;
+import java.util.Collection;
 import java.util.HashMap;
+import java.util.List;
 import java.util.Map;
+import java.util.Objects;
+import java.util.Optional;
 import jdk.jpackage.internal.IOUtils;
 
 
@@ -97,8 +104,83 @@ public void applyTo(PackageTest test) {
         });
     }
 
+    Iterable<TestRun> getTestRuns() {
+        return Optional.ofNullable(testRuns).orElseGet(() -> {
+            return createTestRuns().addTestRunForFilenames("test").testRuns;
+        });
+    }
+
+    public static TestRunsBuilder createTestRuns() {
+        return new TestRunsBuilder();
+    }
+
+    static class TestRun {
+        Iterable<String> getFileNames() {
+            return testFileNames;
+        }
+
+        void openFiles(List<Path> testFiles) throws IOException {
+            switch (invocationType) {
+                case DesktopOpenAssociatedFile:
+                    TKit.trace(String.format("Use desktop to open [%s] file", testFiles.get(0)));
+                    Desktop.getDesktop().open(testFiles.get(0).toFile());
+                    break;
+
+                case WinCommandLine:
+                case WinDesktopOpenContextMenu:
+                    // TBD: implement
+            }
+        }
+
+        private TestRun(Collection<String> testFileNames,
+                InvocationType invocationType) {
+
+            Objects.requireNonNull(invocationType);
+
+            if (testFileNames.size() == 0) {
+                throw new IllegalArgumentException("Empty test file names list");
+            }
+
+            if (invocationType == InvocationType.DesktopOpenAssociatedFile && testFileNames.size() != 1) {
+                throw new IllegalArgumentException("Only one file can be configured for opening with the desktop");
+            }
+
+            this.testFileNames = testFileNames;
+            this.invocationType = invocationType;
+        }
+
+        private final Collection<String> testFileNames;
+        private final InvocationType invocationType;
+    }
+
+    public static class TestRunsBuilder {
+        public TestRunsBuilder setCurrentInvocationType(InvocationType v) {
+            curInvocationType = v;
+            return this;
+        }
+
+        public TestRunsBuilder addTestRunForFilenames(String ... filenames) {
+            testRuns.add(new TestRun(List.of(filenames), curInvocationType));
+            return this;
+        }
+
+        public void applyTo(FileAssociations fa) {
+            fa.testRuns = testRuns;
+        }
+
+        private InvocationType curInvocationType = InvocationType.DesktopOpenAssociatedFile;
+        private List<TestRun> testRuns = new ArrayList<>();
+    }
+
+    public static enum InvocationType {
+        DesktopOpenAssociatedFile,
+        WinCommandLine,
+        WinDesktopOpenContextMenu
+    }
+
     private Path file;
     final private String suffixName;
     private String description;
     private Path icon;
+    private Collection<TestRun> testRuns;
 }
diff --git a/test/jdk/tools/jpackage/helpers/jdk/jpackage/test/LinuxHelper.java b/test/jdk/tools/jpackage/helpers/jdk/jpackage/test/LinuxHelper.java
index 3b45319553dd4..44212587f7dd9 100644
--- a/test/jdk/tools/jpackage/helpers/jdk/jpackage/test/LinuxHelper.java
+++ b/test/jdk/tools/jpackage/helpers/jdk/jpackage/test/LinuxHelper.java
@@ -41,6 +41,7 @@
 import java.util.stream.Collectors;
 import java.util.stream.Stream;
 import jdk.jpackage.internal.IOUtils;
+import jdk.jpackage.test.Functional.ThrowingConsumer;
 import jdk.jpackage.test.PackageTest.PackageHandlers;
 
 
@@ -471,13 +472,24 @@ private static Path getSystemDesktopFilesFolder() {
                 "Failed to locate system .desktop files folder"));
     }
 
+    private static void withTestFileAssociationsFile(FileAssociations fa,
+            ThrowingConsumer<Path> consumer) {
+        boolean iterated[] = new boolean[] { false };
+        PackageTest.withFileAssociationsTestRuns(fa, (testRun, testFiles) -> {
+            if (!iterated[0]) {
+                iterated[0] = true;
+                consumer.accept(testFiles.get(0));
+            }
+        });
+    }
+
     static void addFileAssociationsVerifier(PackageTest test, FileAssociations fa) {
         test.addInstallVerifier(cmd -> {
             if (cmd.isPackageUnpacked("Not running file associations checks")) {
                 return;
             }
 
-            PackageTest.withTestFileAssociationsFile(fa, testFile -> {
+            withTestFileAssociationsFile(fa, testFile -> {
                 String mimeType = queryFileMimeType(testFile);
 
                 TKit.assertEquals(fa.getMime(), mimeType, String.format(
@@ -501,7 +513,7 @@ static void addFileAssociationsVerifier(PackageTest test, FileAssociations fa) {
         });
 
         test.addUninstallVerifier(cmd -> {
-            PackageTest.withTestFileAssociationsFile(fa, testFile -> {
+            withTestFileAssociationsFile(fa, testFile -> {
                 String mimeType = queryFileMimeType(testFile);
 
                 TKit.assertNotEquals(fa.getMime(), mimeType, String.format(
diff --git a/test/jdk/tools/jpackage/helpers/jdk/jpackage/test/PackageTest.java b/test/jdk/tools/jpackage/helpers/jdk/jpackage/test/PackageTest.java
index bd5fd7ca65bd1..a36fc70ef59a2 100644
--- a/test/jdk/tools/jpackage/helpers/jdk/jpackage/test/PackageTest.java
+++ b/test/jdk/tools/jpackage/helpers/jdk/jpackage/test/PackageTest.java
@@ -46,6 +46,7 @@
 import java.util.function.Supplier;
 import java.util.stream.Collectors;
 import java.util.stream.Stream;
+import java.util.stream.StreamSupport;
 import jdk.jpackage.internal.ApplicationLayout;
 import jdk.jpackage.test.Functional.ThrowingBiConsumer;
 import static jdk.jpackage.test.Functional.ThrowingBiConsumer.toBiConsumer;
@@ -227,15 +228,21 @@ public PackageTest disablePackageUninstaller() {
         return this;
     }
 
-    static void withTestFileAssociationsFile(FileAssociations fa,
-            ThrowingConsumer<Path> consumer) {
-        final Path testFileDefaultName = Path.of("test" + fa.getSuffix());
-        TKit.withTempFile(testFileDefaultName, testFile -> {
-            if (TKit.isLinux()) {
-                LinuxHelper.initFileAssociationsTestFile(testFile);
-            }
-            consumer.accept(testFile);
-        });
+    static void withFileAssociationsTestRuns(FileAssociations fa,
+            ThrowingBiConsumer<FileAssociations.TestRun, List<Path>> consumer) {
+        for (var testRun : fa.getTestRuns()) {
+            TKit.withTempDirectory("fa-test-files", tempDir -> {
+                List<Path> testFiles = StreamSupport.stream(testRun.getFileNames().spliterator(), false).map(fname -> {
+                    return tempDir.resolve(fname + fa.getSuffix()).toAbsolutePath().normalize();
+                }).toList();
+
+                if (TKit.isLinux()) {
+                    testFiles.forEach(LinuxHelper::initFileAssociationsTestFile);
+                }
+
+                consumer.accept(testRun, testFiles);
+            });
+        }
     }
 
     PackageTest addHelloAppFileAssociationsVerifier(FileAssociations fa,
@@ -261,21 +268,19 @@ PackageTest addHelloAppFileAssociationsVerifier(FileAssociations fa,
                 return;
             }
 
-            withTestFileAssociationsFile(fa, testFile -> {
-                testFile = testFile.toAbsolutePath().normalize();
-
-                final Path appOutput = testFile.getParent()
+            withFileAssociationsTestRuns(fa, (testRun, testFiles) -> {
+                final Path appOutput = testFiles.get(0).getParent()
                         .resolve(HelloApp.OUTPUT_FILENAME);
                 Files.deleteIfExists(appOutput);
 
-                TKit.trace(String.format("Use desktop to open [%s] file",
-                        testFile));
-                Desktop.getDesktop().open(testFile.toFile());
+                testRun.openFiles(testFiles);
                 TKit.waitForFileCreated(appOutput, 7);
 
                 List<String> expectedArgs = new ArrayList<>(List.of(
                         faLauncherDefaultArgs));
-                expectedArgs.add(testFile.toString());
+                testFiles.forEach(testFile -> {
+                    expectedArgs.add(testFile.toString());
+                });
 
                 // Wait a little bit after file has been created to
                 // make sure there are no pending writes into it.