diff --git a/server/lib/ip.ts b/server/lib/ip.ts
index f9b3cb61..b2ff58d6 100644
--- a/server/lib/ip.ts
+++ b/server/lib/ip.ts
@@ -116,6 +116,68 @@ function bigIntToIp(num: bigint, version: IPVersion): string {
     }
 }
 
+/**
+ * Parses an endpoint string (ip:port) handling both IPv4 and IPv6 addresses.
+ * IPv6 addresses may be bracketed like [::1]:8080 or unbracketed like ::1:8080.
+ * For unbracketed IPv6, the last colon-separated segment is treated as the port.
+ * 
+ * @param endpoint The endpoint string to parse (e.g., "192.168.1.1:8080" or "[::1]:8080" or "2607:fea8::1:8080")
+ * @returns An object with ip and port, or null if parsing fails
+ */
+export function parseEndpoint(endpoint: string): { ip: string; port: number } | null {
+    if (!endpoint) return null;
+
+    // Check for bracketed IPv6 format: [ip]:port
+    const bracketedMatch = endpoint.match(/^\[([^\]]+)\]:(\d+)$/);
+    if (bracketedMatch) {
+        const ip = bracketedMatch[1];
+        const port = parseInt(bracketedMatch[2], 10);
+        if (isNaN(port)) return null;
+        return { ip, port };
+    }
+
+    // Check if this looks like IPv6 (contains multiple colons)
+    const colonCount = (endpoint.match(/:/g) || []).length;
+    
+    if (colonCount > 1) {
+        // This is IPv6 - the port is after the last colon
+        const lastColonIndex = endpoint.lastIndexOf(":");
+        const ip = endpoint.substring(0, lastColonIndex);
+        const portStr = endpoint.substring(lastColonIndex + 1);
+        const port = parseInt(portStr, 10);
+        if (isNaN(port)) return null;
+        return { ip, port };
+    }
+
+    // IPv4 format: ip:port
+    if (colonCount === 1) {
+        const [ip, portStr] = endpoint.split(":");
+        const port = parseInt(portStr, 10);
+        if (isNaN(port)) return null;
+        return { ip, port };
+    }
+
+    return null;
+}
+
+/**
+ * Formats an IP and port into a consistent endpoint string.
+ * IPv6 addresses are wrapped in brackets for proper parsing.
+ * 
+ * @param ip The IP address (IPv4 or IPv6)
+ * @param port The port number
+ * @returns Formatted endpoint string
+ */
+export function formatEndpoint(ip: string, port: number): string {
+    // Check if this is IPv6 (contains colons)
+    if (ip.includes(":")) {
+        // Remove brackets if already present
+        const cleanIp = ip.replace(/^\[|\]$/g, "");
+        return `[${cleanIp}]:${port}`;
+    }
+    return `${ip}:${port}`;
+}
+
 /**
  * Converts CIDR to IP range
  */
diff --git a/server/lib/rebuildClientAssociations.ts b/server/lib/rebuildClientAssociations.ts
index 134cbc06..60384fcf 100644
--- a/server/lib/rebuildClientAssociations.ts
+++ b/server/lib/rebuildClientAssociations.ts
@@ -33,6 +33,8 @@ import {
     generateAliasConfig,
     generateRemoteSubnets,
     generateSubnetProxyTargets,
+    parseEndpoint,
+    formatEndpoint
 } from "@server/lib/ip";
 import {
     addPeerData,
@@ -541,6 +543,13 @@ export async function updateClientSiteDestinations(
             continue;
         }
 
+        // Parse the endpoint properly for both IPv4 and IPv6
+        const parsedEndpoint = parseEndpoint(site.clientSitesAssociationsCache.endpoint);
+        if (!parsedEndpoint) {
+            logger.warn(`Failed to parse endpoint ${site.clientSitesAssociationsCache.endpoint}, skipping`);
+            continue;
+        }
+
         // find the destinations in the array
         let destinations = exitNodeDestinations.find(
             (d) => d.reachableAt === site.exitNodes?.reachableAt
@@ -552,13 +561,8 @@ export async function updateClientSiteDestinations(
                 exitNodeId: site.exitNodes?.exitNodeId || 0,
                 type: site.exitNodes?.type || "",
                 name: site.exitNodes?.name || "",
-                sourceIp:
-                    site.clientSitesAssociationsCache.endpoint.split(":")[0] ||
-                    "",
-                sourcePort:
-                    parseInt(
-                        site.clientSitesAssociationsCache.endpoint.split(":")[1]
-                    ) || 0,
+                sourceIp: parsedEndpoint.ip,
+                sourcePort: parsedEndpoint.port,
                 destinations: [
                     {
                         destinationIP: site.sites.subnet.split("/")[0],
diff --git a/server/routers/gerbil/updateHolePunch.ts b/server/routers/gerbil/updateHolePunch.ts
index e1fa7c4c..3f24430b 100644
--- a/server/routers/gerbil/updateHolePunch.ts
+++ b/server/routers/gerbil/updateHolePunch.ts
@@ -21,6 +21,7 @@ import { validateOlmSessionToken } from "@server/auth/sessions/olm";
 import { checkExitNodeOrg } from "#dynamic/lib/exitNodes";
 import { updatePeer as updateOlmPeer } from "../olm/peers";
 import { updatePeer as updateNewtPeer } from "../newt/peers";
+import { formatEndpoint } from "@server/lib/ip";
 
 // Define Zod schema for request validation
 const updateHolePunchSchema = z.object({
@@ -207,9 +208,12 @@ export async function updateAndGenerateEndpointDestinations(
             //     `Updating site ${site.siteId} on exit node ${exitNode.exitNodeId}`
             // );
 
+            // Format the endpoint properly for both IPv4 and IPv6
+            const formattedEndpoint = formatEndpoint(ip, port);
+
             // if the public key or endpoint has changed, update it otherwise continue
             if (
-                site.endpoint === `${ip}:${port}` &&
+                site.endpoint === formattedEndpoint &&
                 site.publicKey === publicKey
             ) {
                 continue;
@@ -218,7 +222,7 @@ export async function updateAndGenerateEndpointDestinations(
             const [updatedClientSitesAssociationsCache] = await db
                 .update(clientSitesAssociationsCache)
                 .set({
-                    endpoint: `${ip}:${port}`,
+                    endpoint: formattedEndpoint,
                     publicKey: publicKey
                 })
                 .where(
@@ -310,11 +314,14 @@ export async function updateAndGenerateEndpointDestinations(
 
         currentSiteId = newt.siteId;
 
+        // Format the endpoint properly for both IPv4 and IPv6
+        const formattedSiteEndpoint = formatEndpoint(ip, port);
+
         // Update the current site with the new endpoint
         const [updatedSite] = await db
             .update(sites)
             .set({
-                endpoint: `${ip}:${port}`,
+                endpoint: formattedSiteEndpoint,
                 lastHolePunch: timestamp
             })
             .where(eq(sites.siteId, newt.siteId))