diff --git a/package-lock.json b/package-lock.json
index c7e1c2e..4d468c5 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -1,12 +1,12 @@
 {
   "name": "@gitcommit90/rerouted",
-  "version": "0.5.13",
+  "version": "0.5.14",
   "lockfileVersion": 3,
   "requires": true,
   "packages": {
     "": {
       "name": "@gitcommit90/rerouted",
-      "version": "0.5.13",
+      "version": "0.5.14",
       "license": "MIT",
       "bin": {
         "rerouted": "src/cli/index.js"
diff --git a/package.json b/package.json
index b0fd69a..043afc5 100644
--- a/package.json
+++ b/package.json
@@ -1,7 +1,7 @@
 {
   "name": "@gitcommit90/rerouted",
   "productName": "ReRouted",
-  "version": "0.5.13",
+  "version": "0.5.14",
   "description": "A local AI router for connected accounts, models, named routes, and automatic fallback.",
   "author": "gitcommit90",
   "license": "MIT",
diff --git a/src/lib/providers/claude.js b/src/lib/providers/claude.js
index c052b4e..b9c710f 100644
--- a/src/lib/providers/claude.js
+++ b/src/lib/providers/claude.js
@@ -109,21 +109,19 @@ function generateBillingHeader(payload) {
 }
 
 /**
- * Strip third-party agent structure that can trigger extra-usage or proxy
- * detection on OAuth traffic.
+ * Preserve client system context while moving it into the provider-compatible
+ * reminder location used for OAuth traffic. Truncating this text is unsafe:
+ * callers rely on late system blocks for policy, memory, and handoff state.
  */
 function sanitizeForwardedSystemPrompt(text) {
-  if (!String(text || "").trim()) return "";
-  // Keep a short neutral reminder; full client system prompts look like non-CLI agents.
+  const forwarded = String(text || "").trim();
+  if (!forwarded) return "";
   return [
     "Use the available tools when needed to help with software engineering tasks.",
     "Keep responses concise and focused on the user's request.",
     "Prefer acting on the user's task over describing product-specific workflows.",
-    // Preserve a short slice of original context if useful
-    String(text).trim().slice(0, 400),
-  ]
-    .filter(Boolean)
-    .join("\n");
+    forwarded,
+  ].join("\n");
 }
 
 /** Wrap forwarded system context in provider-compatible reminder blocks. */
diff --git a/tests/gateway.test.js b/tests/gateway.test.js
index 472bc7b..96a845a 100644
--- a/tests/gateway.test.js
+++ b/tests/gateway.test.js
@@ -745,10 +745,12 @@ describe("OAuth refresh against mock", () => {
 
 describe("claude oauth request shaping", () => {
   it("applyCloaking injects CC system blocks + metadata; moves client system to user", () => {
+    const lateSystemSentinel = `LATE_SYSTEM_HANDOFF_${"z".repeat(1600)}_END`;
     const base = claude.toAnthropicBody(
       {
         messages: [
           { role: "system", content: "You are a custom app agent with secret tools." },
+          { role: "system", content: lateSystemSentinel },
           { role: "user", content: "hi" },
         ],
         max_tokens: 8,
@@ -774,6 +776,9 @@ describe("claude oauth request shaping", () => {
       ? userContent.map((b) => b.text || "").join("\n")
       : String(userContent);
     assert.ok(userText.includes("<system-reminder>"), userText.slice(0, 200));
+    assert.ok(userText.includes("You are a custom app agent with secret tools."));
+    assert.ok(userText.includes(lateSystemSentinel), "late and long client system context must survive OAuth request shaping");
+    assert.ok(userText.includes(`${lateSystemSentinel}\n\nIMPORTANT:`), "the complete sentinel must precede the reminder footer");
     const uid = JSON.parse(cloaked.metadata.user_id);
     assert.equal(uid.session_id, sessionId);
     assert.ok(uid.device_id && uid.account_uuid);