diff --git a/CHANGELOG.md b/CHANGELOG.md
index 8f05c324..51005576 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,3 +1,4 @@
+- Fixed ChatGPT Subscription token refresh hanging indefinitely (freezing the session) when a profile's custom HTTPS/HTTP proxy hostname was slow or unreachable to resolve via DNS
 - Fixed a choice-dialog prompt (e.g. a Bash-command permission prompt) flickering and repeatedly resizing when Claude's response text re-wrapped to a slightly different width after the dialog first appeared
 
 # 1.3.12 (2026-09-27)
diff --git a/pom.xml b/pom.xml
index 8ecbe430..98a0e36c 100644
--- a/pom.xml
+++ b/pom.xml
@@ -6,7 +6,7 @@
 
     <groupId>io.github.nbplugins</groupId>
     <artifactId>netbeans-plugin-claude-code-gui</artifactId>
-    <version>1.3.32-SNAPSHOT</version>
+    <version>1.3.33-SNAPSHOT</version>
     <packaging>nbm</packaging>
     <name>Netbeans Plugin Claude Code GUI</name>
     <description>NetBeans plugin that provides a GUI for Claude Code CLI — run claude code sessions directly inside the IDE.</description>
diff --git a/src/main/java/io/github/nbplugins/claudecodegui/settings/ProxyConfiguration.java b/src/main/java/io/github/nbplugins/claudecodegui/settings/ProxyConfiguration.java
index 718d7289..82973127 100644
--- a/src/main/java/io/github/nbplugins/claudecodegui/settings/ProxyConfiguration.java
+++ b/src/main/java/io/github/nbplugins/claudecodegui/settings/ProxyConfiguration.java
@@ -63,7 +63,7 @@ public HttpClient.Builder applyTo(HttpClient.Builder builder) {
                     try {
                         URI uri  = URI.create(url);
                         int port = uri.getPort() > 0 ? uri.getPort() : 8080;
-                        builder.proxy(ProxySelector.of(new InetSocketAddress(uri.getHost(), port)));
+                        builder.proxy(ProxySelector.of(InetSocketAddress.createUnresolved(uri.getHost(), port)));
                     } catch (Exception e) {
                         builder.proxy(ProxySelector.getDefault());
                     }
diff --git a/src/test/java/io/github/nbplugins/claudecodegui/settings/ProxyConfigurationTest.java b/src/test/java/io/github/nbplugins/claudecodegui/settings/ProxyConfigurationTest.java
new file mode 100644
index 00000000..d087b1e0
--- /dev/null
+++ b/src/test/java/io/github/nbplugins/claudecodegui/settings/ProxyConfigurationTest.java
@@ -0,0 +1,105 @@
+package io.github.nbplugins.claudecodegui.settings;
+
+import io.github.nbplugins.claudecodegui.settings.ClaudeProfile.ProxyMode;
+import java.net.InetSocketAddress;
+import java.net.URI;
+import java.net.http.HttpClient;
+import java.time.Duration;
+import org.junit.jupiter.api.Test;
+import static org.junit.jupiter.api.Assertions.*;
+
+/**
+ * Unit tests for {@link ProxyConfiguration}.
+ */
+class ProxyConfigurationTest {
+
+    // -------------------------------------------------------------------------
+    // applyTo — CUSTOM proxy must not eagerly resolve the proxy hostname
+    // -------------------------------------------------------------------------
+
+    /**
+     * Regression: {@code new InetSocketAddress(host, port)} resolves the hostname via
+     * a blocking DNS lookup at construction time. If the proxy host cannot be resolved
+     * (unreachable DNS, typo, VPN down), this hangs the calling thread indefinitely —
+     * observed as {@link io.github.nbplugins.claudecodegui.chatgptauth.ChatGptTokenManager#refresh}
+     * hanging forever in {@code ChatGptTokenManagerTest}. The proxy address must be built
+     * with {@link InetSocketAddress#createUnresolved} so resolution is deferred to actual
+     * connection time (subject to the HTTP client's own connect timeout).
+     */
+    @Test
+    void applyTo_customProxy_doesNotEagerlyResolveHostname() {
+        ProxyConfiguration cfg = new ProxyConfiguration(
+                ProxyMode.CUSTOM, "", "http://proxy.example.invalid:3128", "");
+
+        HttpClient client = cfg.applyTo(HttpClient.newBuilder()).build();
+
+        assertTrue(client.proxy().isPresent(), "proxy must be configured");
+        InetSocketAddress addr = (InetSocketAddress) client.proxy().get()
+                .select(URI.create("https://api.openai.com")).get(0).address();
+
+        assertTrue(addr.isUnresolved(),
+                "proxy address must be unresolved — eager resolution can hang the calling thread");
+        assertEquals("proxy.example.invalid", addr.getHostString());
+        assertEquals(3128, addr.getPort());
+    }
+
+    /**
+     * Regression reproduction of the actual hang: an existing, real hostname whose DNS
+     * query hangs (rather than failing fast with NXDOMAIN like a made-up TLD does) must
+     * not block {@code applyTo}. This is the exact hostname used in the original hanging
+     * test ({@code ChatGptTokenManagerTest.refresh_usesHttpClientConfiguredWithProfileProxySettings}).
+     * On the old {@code new InetSocketAddress(host, port)} code this call hangs
+     * indefinitely in sandboxes where DNS queries for real-but-unreachable hosts are
+     * dropped rather than rejected; {@code assertTimeoutPreemptively} turns that hang
+     * into a fast test failure instead of stalling the whole suite.
+     */
+    @Test
+    void applyTo_customProxy_doesNotHangOnSlowOrDroppedDnsQuery() {
+        ProxyConfiguration cfg = new ProxyConfiguration(
+                ProxyMode.CUSTOM, "", "http://proxy.example.com:3128", "");
+
+        assertTimeoutPreemptively(Duration.ofSeconds(5), () -> {
+            HttpClient client = cfg.applyTo(HttpClient.newBuilder()).build();
+            InetSocketAddress addr = (InetSocketAddress) client.proxy().orElseThrow()
+                    .select(URI.create("https://api.openai.com")).get(0).address();
+            assertTrue(addr.isUnresolved(), "proxy address must be unresolved");
+        });
+    }
+
+    @Test
+    void applyTo_customProxy_defaultPortWhenNoneSpecified() {
+        ProxyConfiguration cfg = new ProxyConfiguration(
+                ProxyMode.CUSTOM, "", "http://proxy.example.invalid", "");
+
+        HttpClient client = cfg.applyTo(HttpClient.newBuilder()).build();
+
+        InetSocketAddress addr = (InetSocketAddress) client.proxy().orElseThrow()
+                .select(URI.create("https://api.openai.com")).get(0).address();
+        assertEquals(8080, addr.getPort());
+    }
+
+    @Test
+    void applyTo_customProxy_fallsBackToHttpProxyWhenHttpsProxyBlank() {
+        ProxyConfiguration cfg = new ProxyConfiguration(
+                ProxyMode.CUSTOM, "http://proxy.example.invalid:3129", "", "");
+
+        HttpClient client = cfg.applyTo(HttpClient.newBuilder()).build();
+
+        InetSocketAddress addr = (InetSocketAddress) client.proxy().orElseThrow()
+                .select(URI.create("https://api.openai.com")).get(0).address();
+        assertEquals("proxy.example.invalid", addr.getHostString());
+        assertEquals(3129, addr.getPort());
+    }
+
+    @Test
+    void applyTo_noProxy_disablesProxying() {
+        ProxyConfiguration cfg = new ProxyConfiguration(ProxyMode.NO_PROXY, "", "", "");
+
+        HttpClient client = cfg.applyTo(HttpClient.newBuilder()).build();
+
+        boolean noProxySelected = client.proxy().isEmpty() || client.proxy().get()
+                .select(URI.create("https://api.openai.com")).stream()
+                .allMatch(p -> p.type() == java.net.Proxy.Type.DIRECT);
+        assertTrue(noProxySelected, "NO_PROXY must not select any proxy address");
+    }
+}