diff --git a/packages/core/src/utils/dsn.ts b/packages/core/src/utils/dsn.ts
index 492f2398c390..435927688617 100644
--- a/packages/core/src/utils/dsn.ts
+++ b/packages/core/src/utils/dsn.ts
@@ -7,7 +7,7 @@ import { consoleSandbox, debug } from './debug-logger';
 const ORG_ID_REGEX = /^o(\d+)\./;
 
 /** Regular expression used to parse a Dsn. */
-const DSN_REGEX = /^(?:(\w+):)\/\/(?:(\w+)(?::(\w+)?)?@)([\w.-]+)(?::(\d+))?\/(.+)/;
+const DSN_REGEX = /^(?:(\w+):)\/\/(?:(\w+)(?::(\w+)?)?@)((?:\[[0-9a-fA-F:]+\]|[\w.-]+))(?::(\d+))?\/(.+)/;
 
 function isValidProtocol(protocol?: string): protocol is DsnProtocol {
   return protocol === 'http' || protocol === 'https';
diff --git a/packages/node-core/src/transports/http.ts b/packages/node-core/src/transports/http.ts
index 49897dfa22b1..18a8a558ae0a 100644
--- a/packages/node-core/src/transports/http.ts
+++ b/packages/node-core/src/transports/http.ts
@@ -127,12 +127,15 @@ function createRequestExecutor(
           body = body.pipe(createGzip());
         }
 
+        const hostnameIsIPv6 = hostname.startsWith('[');
+
         const req = httpModule.request(
           {
             method: 'POST',
             agent,
             headers,
-            hostname,
+            // Remove "[" and "]" from IPv6 hostnames
+            hostname: hostnameIsIPv6 ? hostname.slice(1, -1) : hostname,
             path: `${pathname}${search}`,
             port,
             protocol,