diff --git a/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/configuration/WebserverConfiguration.java b/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/configuration/WebserverConfiguration.java
index cf5884485..ed6c00d34 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/configuration/WebserverConfiguration.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/configuration/WebserverConfiguration.java
@@ -107,4 +107,8 @@ public class WebserverConfiguration {
     public String getAlias() {
         return config.get(WebserverSettings.CERTIFICATE_ALIAS);
     }
+
+    public boolean isProxyModeHttps() {
+        return "proxy".equals(config.get(WebserverSettings.CERTIFICATE_PATH));
+    }
 }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/http/JettyWebserver.java b/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/http/JettyWebserver.java
index ce59ee6ee..6244e17e9 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/http/JettyWebserver.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/http/JettyWebserver.java
@@ -100,7 +100,11 @@ public class JettyWebserver implements WebServer {
                     return new ServerConnector(webserver, sslContextFactory, alpn, httpConnector, http2Connector, http2CConnector);
                 })
                 .orElseGet(() -> {
-                    webserverLogMessages.authenticationNotPossible();
+                    if (webserverConfiguration.isProxyModeHttps()) {
+                        webserverLogMessages.authenticationUsingProxy();
+                    } else {
+                        webserverLogMessages.authenticationNotPossible();
+                    }
                     return new ServerConnector(webserver, httpConnector, http2CConnector);
                 });
 
@@ -146,12 +150,11 @@ public class JettyWebserver implements WebServer {
     }
 
     private Optional<SslContextFactory.Server> getSslContextFactory() {
-        String keyStorePath = webserverConfiguration.getKeyStorePath();
-        if ("proxy".equals(keyStorePath)) {
-            webserverLogMessages.authenticationUsingProxy();
+        if (webserverConfiguration.isProxyModeHttps()) {
             return Optional.empty();
         }
 
+        String keyStorePath = webserverConfiguration.getKeyStorePath();
         if (!new File(keyStorePath).exists()) {
             webserverLogMessages.keystoreFileNotFound();
             return Optional.empty();
@@ -207,7 +210,7 @@ public class JettyWebserver implements WebServer {
 
     @Override
     public boolean isUsingHTTPS() {
-        return usingHttps;
+        return usingHttps || webserverConfiguration.isProxyModeHttps();
     }
 
     @Override
diff --git a/Plan/common/src/test/java/com/djrapitops/plan/delivery/webserver/ProxyModeHttpsTest.java b/Plan/common/src/test/java/com/djrapitops/plan/delivery/webserver/ProxyModeHttpsTest.java
new file mode 100644
index 000000000..600f03164
--- /dev/null
+++ b/Plan/common/src/test/java/com/djrapitops/plan/delivery/webserver/ProxyModeHttpsTest.java
@@ -0,0 +1,65 @@
+/*
+ *  This file is part of Player Analytics (Plan).
+ *
+ *  Plan is free software: you can redistribute it and/or modify
+ *  it under the terms of the GNU Lesser General Public License v3 as published by
+ *  the Free Software Foundation, either version 3 of the License, or
+ *  (at your option) any later version.
+ *
+ *  Plan is distributed in the hope that it will be useful,
+ *  but WITHOUT ANY WARRANTY; without even the implied warranty of
+ *  MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ *  GNU Lesser General Public License for more details.
+ *
+ *  You should have received a copy of the GNU Lesser General Public License
+ *  along with Plan. If not, see <https://www.gnu.org/licenses/>.
+ */
+package com.djrapitops.plan.delivery.webserver;
+
+import com.djrapitops.plan.PlanSystem;
+import com.djrapitops.plan.settings.config.PlanConfig;
+import com.djrapitops.plan.settings.config.paths.WebserverSettings;
+import org.junit.jupiter.api.AfterAll;
+import org.junit.jupiter.api.BeforeAll;
+import org.junit.jupiter.api.DisplayName;
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.io.TempDir;
+import utilities.RandomData;
+import utilities.mocks.PluginMockComponent;
+
+import java.nio.file.Path;
+
+import static org.junit.jupiter.api.Assertions.assertEquals;
+
+class ProxyModeHttpsTest {
+    private static final int TEST_PORT_NUMBER = RandomData.randomInt(9005, 9500);
+
+    private static PlanSystem system;
+
+    @BeforeAll
+    static void setUpClass(@TempDir Path tempDir) throws Exception {
+        PluginMockComponent component = new PluginMockComponent(tempDir);
+        system = component.getPlanSystem();
+
+        PlanConfig config = system.getConfigSystem().getConfig();
+
+        config.set(WebserverSettings.CERTIFICATE_PATH, "proxy");
+
+        config.set(WebserverSettings.PORT, TEST_PORT_NUMBER);
+
+        system.enable();
+    }
+
+    @AfterAll
+    static void tearDownClass() {
+        if (system != null) {
+            system.disable();
+        }
+    }
+
+    @Test
+    @DisplayName("Webserver with 'proxy' keystore path assumes proxy server is handling https")
+    void proxyModeAddressIsHttps() {
+        assertEquals("https", system.getWebServerSystem().getWebServer().getProtocol());
+    }
+}