Add test asserting that outdated dependencies of detached plugins are updated

test/src/test/java/jenkins/install/LoadDetachedPluginsTest.java

@@ -31,7 +31,6 @@ import hudson.PluginManager;
 import hudson.PluginManagerUtil;
 import hudson.PluginWrapper;
 import hudson.util.VersionNumber;
-import java.io.File;
 import java.io.IOException;
 import java.util.ArrayList;
 import java.util.List;
@@ -87,7 +86,7 @@ public class LoadDetachedPluginsTest {
     @Issue("JENKINS-48604")
     @Test
     @LocalData
-    public void upgradeFromJenkins2WithDependency() {
+    public void upgradeFromJenkins2WithNewerDependency() {
         VersionNumber since = new VersionNumber("2.0");
         rr.then(r -> {
             List<DetachedPlugin> detachedPlugins = ClassicPluginStrategy.getDetachedPlugins(since);
@@ -98,7 +97,25 @@ public class LoadDetachedPluginsTest {
             Plugin scriptSecurity = r.jenkins.getPlugin("script-security");
             assertThat("Script-security should be installed", scriptSecurity, notNullValue());
             assertThat("Dependencies of detached plugins should not be downgraded",
-                    scriptSecurity.getWrapper().getVersionNumber(), greaterThan(new VersionNumber("1.18.1")));
+                    scriptSecurity.getWrapper().getVersionNumber(), equalTo(new VersionNumber("1.34")));
+            assertNoFailedPlugins(r);
+        });
+    }
+
+    @Test
+    @LocalData
+    public void upgradeFromJenkins2WithOlderDependency() {
+        VersionNumber since = new VersionNumber("2.0");
+        rr.then(r -> {
+            List<DetachedPlugin> detachedPlugins = ClassicPluginStrategy.getDetachedPlugins(since);
+            assertThat("Plugins have been detached since the pre-upgrade version",
+                    detachedPlugins.size(), greaterThan(1));
+            assertThat("Plugins detached between the pre-upgrade version and the current version should be installed",
+                    getInstalledDetachedPlugins(r, detachedPlugins).size(), equalTo(detachedPlugins.size()));
+            Plugin scriptSecurity = r.jenkins.getPlugin("script-security");
+            assertThat("Script-security should be installed", scriptSecurity, notNullValue());
+            assertThat("Dependencies of detached plugins should be upgraded to the required version",
+                    scriptSecurity.getWrapper().getVersionNumber(), equalTo(new VersionNumber("1.18.1")));
             assertNoFailedPlugins(r);
         });
     }