diff --git a/proxy/src/test/java/com/velocitypowered/proxy/plugin/util/PluginDependencyUtilsTest.java b/proxy/src/test/java/com/velocitypowered/proxy/plugin/util/PluginDependencyUtilsTest.java
index 99033c689..5709b2864 100644
--- a/proxy/src/test/java/com/velocitypowered/proxy/plugin/util/PluginDependencyUtilsTest.java
+++ b/proxy/src/test/java/com/velocitypowered/proxy/plugin/util/PluginDependencyUtilsTest.java
@@ -14,49 +14,64 @@ import org.junit.jupiter.api.Test;
 
 class PluginDependencyUtilsTest {
 
-  private static final PluginDescription NO_DEPENDENCY_1_EXAMPLE = testDescription("example");
-  private static final PluginDescription NEVER_DEPENDED = testDescription("and-again");
-  private static final PluginDescription SOFT_DEPENDENCY_EXISTS = testDescription("soft",
-      ImmutableList.of(new PluginDependency("example", "", true)));
-  private static final PluginDescription SOFT_DEPENDENCY_DOES_NOT_EXIST = testDescription("fluffy",
-      ImmutableList.of(new PluginDependency("i-dont-exist", "", false)));
-  private static final PluginDescription MULTI_DEPENDENCY = testDescription("multi-depend",
-      ImmutableList.of(
-          new PluginDependency("example", "", false)
-      )
-  );
-  private static final PluginDescription TEST_WITH_DUPLICATE_DEPEND = testDescription("dup-depend",
-      ImmutableList.of(
-          new PluginDependency("multi-depend", "", false)
-      )
-  );
+  private static final PluginDescription NO_DEPENDENCY = testDescription("trivial");
+  private static final PluginDescription NO_DEPENDENCY_2 = testDescription("trivial2");
+  private static final PluginDescription HAS_DEPENDENCY_1 = testDescription("dependent1",
+      new PluginDependency("trivial", null, false));
+  private static final PluginDescription HAS_DEPENDENCY_2 = testDescription("dependent2",
+      new PluginDependency("dependent1", null, false));
+  private static final PluginDescription HAS_DEPENDENCY_3 = testDescription("dependent3",
+      new PluginDependency("trivial", null, false));
 
   private static final PluginDescription CIRCULAR_DEPENDENCY_1 = testDescription("circle",
-      ImmutableList.of(new PluginDependency("oval", "", false)));
+      new PluginDependency("oval", "", false));
   private static final PluginDescription CIRCULAR_DEPENDENCY_2 = testDescription("oval",
-      ImmutableList.of(new PluginDependency("circle", "", false)));
-
-  private static final ImmutableList<PluginDescription> EXPECTED = ImmutableList.of(
-      NEVER_DEPENDED,
-      NO_DEPENDENCY_1_EXAMPLE,
-      MULTI_DEPENDENCY,
-      TEST_WITH_DUPLICATE_DEPEND,
-      SOFT_DEPENDENCY_DOES_NOT_EXIST,
-      SOFT_DEPENDENCY_EXISTS
-  );
+      new PluginDependency("circle", "", false));
 
   @Test
-  void sortCandidates() throws Exception {
+  void sortCandidatesTrivial() throws Exception {
     List<PluginDescription> descriptionList = new ArrayList<>();
-    descriptionList.add(NO_DEPENDENCY_1_EXAMPLE);
-    descriptionList.add(NEVER_DEPENDED);
-    descriptionList.add(SOFT_DEPENDENCY_DOES_NOT_EXIST);
-    descriptionList.add(SOFT_DEPENDENCY_EXISTS);
-    descriptionList.add(MULTI_DEPENDENCY);
-    descriptionList.add(TEST_WITH_DUPLICATE_DEPEND);
-    descriptionList.sort(Comparator.comparing(PluginDescription::getId));
+    assertEquals(descriptionList, PluginDependencyUtils.sortCandidates(descriptionList));
+  }
 
-    assertEquals(EXPECTED, PluginDependencyUtils.sortCandidates(descriptionList));
+  @Test
+  void sortCandidatesSingleton() throws Exception {
+    List<PluginDescription> plugins = ImmutableList.of(NO_DEPENDENCY);
+    assertEquals(plugins, PluginDependencyUtils.sortCandidates(plugins));
+  }
+
+  @Test
+  void sortCandidatesBasicDependency() throws Exception {
+    List<PluginDescription> plugins = ImmutableList.of(HAS_DEPENDENCY_1, NO_DEPENDENCY);
+    List<PluginDescription> expected = ImmutableList.of(NO_DEPENDENCY, HAS_DEPENDENCY_1);
+    assertEquals(expected, PluginDependencyUtils.sortCandidates(plugins));
+  }
+
+  @Test
+  void sortCandidatesNestedDependency() throws Exception {
+    List<PluginDescription> plugins = ImmutableList.of(HAS_DEPENDENCY_1, HAS_DEPENDENCY_2,
+        NO_DEPENDENCY);
+    List<PluginDescription> expected = ImmutableList.of(NO_DEPENDENCY, HAS_DEPENDENCY_1,
+        HAS_DEPENDENCY_2);
+    assertEquals(expected, PluginDependencyUtils.sortCandidates(plugins));
+  }
+
+  @Test
+  void sortCandidatesTypical() throws Exception {
+    List<PluginDescription> plugins = ImmutableList.of(HAS_DEPENDENCY_2, NO_DEPENDENCY_2,
+        HAS_DEPENDENCY_1, NO_DEPENDENCY);
+    List<PluginDescription> expected = ImmutableList.of(NO_DEPENDENCY, HAS_DEPENDENCY_1,
+        HAS_DEPENDENCY_2, NO_DEPENDENCY_2);
+    assertEquals(expected, PluginDependencyUtils.sortCandidates(plugins));
+  }
+
+  @Test
+  void sortCandidatesMultiplePluginsDependentOnOne() throws Exception {
+    List<PluginDescription> plugins = ImmutableList.of(HAS_DEPENDENCY_3, HAS_DEPENDENCY_1,
+        NO_DEPENDENCY);
+    List<PluginDescription> expected = ImmutableList.of(NO_DEPENDENCY, HAS_DEPENDENCY_3,
+        HAS_DEPENDENCY_1);
+    assertEquals(expected, PluginDependencyUtils.sortCandidates(plugins));
   }
 
   @Test
@@ -65,14 +80,10 @@ class PluginDependencyUtilsTest {
     assertThrows(IllegalStateException.class, () -> PluginDependencyUtils.sortCandidates(descs));
   }
 
-  private static PluginDescription testDescription(String id) {
-    return testDescription(id, ImmutableList.of());
-  }
-
-  private static PluginDescription testDescription(String id, List<PluginDependency> dependencies) {
+  private static PluginDescription testDescription(String id, PluginDependency... dependencies) {
     return new VelocityPluginDescription(
         id, "tuxed", "0.1", null, null, ImmutableList.of(),
-        dependencies, null
+        ImmutableList.copyOf(dependencies), null
     );
   }
 }