diff --git a/Plan/common/src/main/java/com/djrapitops/plan/system/processing/Processing.java b/Plan/common/src/main/java/com/djrapitops/plan/system/processing/Processing.java
index 9f6c0ac2a..7592f8508 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/system/processing/Processing.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/system/processing/Processing.java
@@ -145,15 +145,18 @@ public class Processing implements SubSystem {
                 errorHandler.log(L.WARN, this.getClass(), e);
             }
         }
-        if (!nonCriticalExecutor.isTerminated()) {
-            try {
-                nonCriticalExecutor.awaitTermination(1, TimeUnit.SECONDS);
-            } catch (InterruptedException e) {
+        try {
+            if (!nonCriticalExecutor.isTerminated() && !nonCriticalExecutor.awaitTermination(1, TimeUnit.SECONDS)) {
                 nonCriticalExecutor.shutdownNow();
             }
-        }
-        if (!criticalExecutor.isTerminated()) {
+            if (!criticalExecutor.isTerminated()) {
+                criticalExecutor.shutdownNow();
+            }
+        } catch (InterruptedException e) {
+            logger.error("Processing shutdown thread interrupted: " + e.getMessage());
+            nonCriticalExecutor.shutdownNow();
             criticalExecutor.shutdownNow();
+            Thread.currentThread().interrupt();
         }
         logger.info(locale.get().getString(PluginLang.DISABLED_PROCESSING_COMPLETE));
     }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/system/webserver/WebServer.java b/Plan/common/src/main/java/com/djrapitops/plan/system/webserver/WebServer.java
index a8dedc10d..1b96b28f3 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/system/webserver/WebServer.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/system/webserver/WebServer.java
@@ -258,9 +258,12 @@ public class WebServer implements SubSystem {
             ExecutorService service = (ExecutorService) executor;
             service.shutdown();
             try {
-                service.awaitTermination(5, TimeUnit.SECONDS);
-            } catch (InterruptedException timeoutExceededEx) {
-                service.shutdownNow();
+                if (!service.awaitTermination(5, TimeUnit.SECONDS)) {
+                    service.shutdownNow();
+                }
+            } catch (InterruptedException e) {
+                logger.error("WebServer ExecutorService shutdown thread interrupted on disable: " + e.getMessage());
+                Thread.currentThread().interrupt();
             }
         }
     }