diff --git a/app/main-axios.ts b/app/main-axios.ts
index d633a55..ade06c1 100644
--- a/app/main-axios.ts
+++ b/app/main-axios.ts
@@ -2210,6 +2210,37 @@ function extractJwtFromSetCookie(headers: any): string | null {
   return null;
 }
 
+function isLocalNetworkHttpsUrl(url: string): boolean {
+  if (!url.startsWith("https://")) return false;
+
+  try {
+    const host = new URL(url).hostname.replace(/^\[|\]$/g, "");
+    if (host === "localhost" || host === "::1") return true;
+
+    const parts = host.split(".").map((part) => Number(part));
+    if (parts.length !== 4 || parts.some((part) => !Number.isInteger(part))) {
+      return false;
+    }
+
+    const [first, second] = parts;
+    return (
+      first === 10 ||
+      first === 127 ||
+      (first === 169 && second === 254) ||
+      (first === 172 && second >= 16 && second <= 31) ||
+      (first === 192 && second === 168)
+    );
+  } catch {
+    return false;
+  }
+}
+
+function isNativeNetworkFailure(error: unknown): boolean {
+  return (
+    error instanceof Error && error.message.includes("Network request failed")
+  );
+}
+
 /**
  * Detects whether the server URL sits behind a reverse-proxy authentication
  * gate (Cloudflare Access, Authelia, etc.) that intercepts requests and serves
@@ -2272,11 +2303,23 @@ async function loginWithFetch(
   password: string,
 ): Promise<{ data: any; token: string | null }> {
   const url = `${baseUrl.replace(/\/$/, "")}/users/login`;
-  const fetchResponse = await fetch(url, {
-    method: "POST",
-    headers: { "Content-Type": "application/json" },
-    body: JSON.stringify({ username, password }),
-  });
+  let fetchResponse: Response;
+  try {
+    fetchResponse = await fetch(url, {
+      method: "POST",
+      headers: { "Content-Type": "application/json" },
+      body: JSON.stringify({ username, password }),
+    });
+  } catch (error) {
+    if (isLocalNetworkHttpsUrl(url) && isNativeNetworkFailure(error)) {
+      throw new ApiError(
+        "The app could not trust HTTPS for this local IP. Use a DNS name with a valid certificate, a certificate for this IP, or HTTP on a trusted local/VPN network.",
+        0,
+        "LOCAL_IP_HTTPS_CERTIFICATE_ERROR",
+      );
+    }
+    throw error;
+  }
 
   const contentType = (
     fetchResponse.headers.get("content-type") || ""
diff --git a/plugins/withNetworkSecurityConfig.js b/plugins/withNetworkSecurityConfig.js
index 1266957..8851ecb 100644
--- a/plugins/withNetworkSecurityConfig.js
+++ b/plugins/withNetworkSecurityConfig.js
@@ -5,6 +5,27 @@ const {
 const path = require("path");
 const fs = require("fs");
 
+const NETWORK_SECURITY_CONFIG = `<?xml version="1.0" encoding="utf-8"?>
+<network-security-config>
+    <base-config cleartextTrafficPermitted="true">
+        <trust-anchors>
+            <certificates src="system" />
+            <certificates src="user" />
+        </trust-anchors>
+    </base-config>
+
+    <domain-config cleartextTrafficPermitted="true">
+        <domain includeSubdomains="true">localhost</domain>
+        <domain includeSubdomains="true">127.0.0.1</domain>
+        <domain includeSubdomains="true">10.0.2.2</domain>
+        <trust-anchors>
+            <certificates src="system" />
+            <certificates src="user" />
+        </trust-anchors>
+    </domain-config>
+</network-security-config>
+`;
+
 const withNetworkSecurityConfig = (config) => {
   config = withAndroidManifest(config, async (config) => {
     const mainApplication = config.modResults.manifest.application[0];
@@ -38,28 +59,7 @@ const withNetworkSecurityConfig = (config) => {
         "network_security_config.xml",
       );
 
-      const networkSecurityConfig = `<?xml version="1.0" encoding="utf-8"?>
-<network-security-config>
-    <base-config cleartextTrafficPermitted="true">
-        <trust-anchors>
-            <certificates src="system" />
-            <certificates src="user" />
-        </trust-anchors>
-    </base-config>
-
-    <domain-config cleartextTrafficPermitted="true">
-        <domain includeSubdomains="true">localhost</domain>
-        <domain includeSubdomains="true">127.0.0.1</domain>
-        <domain includeSubdomains="true">10.0.2.2</domain>
-        <trust-anchors>
-            <certificates src="system" />
-            <certificates src="user" />
-        </trust-anchors>
-    </domain-config>
-</network-security-config>
-`;
-
-      fs.writeFileSync(networkSecurityConfigPath, networkSecurityConfig);
+      fs.writeFileSync(networkSecurityConfigPath, NETWORK_SECURITY_CONFIG);
 
       return config;
     },
@@ -69,3 +69,4 @@ const withNetworkSecurityConfig = (config) => {
 };
 
 module.exports = withNetworkSecurityConfig;
+module.exports.NETWORK_SECURITY_CONFIG = NETWORK_SECURITY_CONFIG;