diff --git a/src/proxy/middleware/request/preprocessors/count-prompt-tokens.ts b/src/proxy/middleware/request/preprocessors/count-prompt-tokens.ts
index a621753..130bedf 100644
--- a/src/proxy/middleware/request/preprocessors/count-prompt-tokens.ts
+++ b/src/proxy/middleware/request/preprocessors/count-prompt-tokens.ts
@@ -31,7 +31,10 @@ export const countPromptTokens: RequestPreprocessor = async (req) => {
     }
     case "anthropic-chat": {
       req.outputTokens = req.body.max_tokens;
-      const prompt: AnthropicChatMessage[] = req.body.messages;
+      const prompt = {
+        system: req.body.system ?? "",
+        messages: req.body.messages,
+      };
       result = await countTokens({ req, prompt, service });
       break;
     }
diff --git a/src/proxy/middleware/request/preprocessors/validate-context-size.ts b/src/proxy/middleware/request/preprocessors/validate-context-size.ts
index 127e60d..dd62212 100644
--- a/src/proxy/middleware/request/preprocessors/validate-context-size.ts
+++ b/src/proxy/middleware/request/preprocessors/validate-context-size.ts
@@ -46,6 +46,11 @@ export const validateContextSize: RequestPreprocessor = async (req) => {
   }
   proxyMax ||= Number.MAX_SAFE_INTEGER;
 
+  if (req.user?.type === "special") {
+    req.log.debug("Special user, not enforcing proxy context limit.");
+    proxyMax = Number.MAX_SAFE_INTEGER;
+  }
+
   let modelMax: number;
   if (model.match(/gpt-3.5-turbo-16k/)) {
     modelMax = 16384;
diff --git a/src/proxy/middleware/response/index.ts b/src/proxy/middleware/response/index.ts
index 83a2a68..667b89e 100644
--- a/src/proxy/middleware/response/index.ts
+++ b/src/proxy/middleware/response/index.ts
@@ -370,7 +370,7 @@ async function handleAnthropicBadRequestError(
       "Anthropic key has been disabled."
     );
     keyPool.disable(req.key!, "revoked");
-    errorPayload.proxy_note = `Assigned key has been disabled. ${error?.message}`;
+    errorPayload.proxy_note = `Assigned key has been disabled. (${error?.message})`;
     return;
   }
 
diff --git a/src/shared/tokenization/claude.ts b/src/shared/tokenization/claude.ts
index fa32eff..880db82 100644
--- a/src/shared/tokenization/claude.ts
+++ b/src/shared/tokenization/claude.ts
@@ -19,7 +19,9 @@ export function init() {
   return true;
 }
 
-export async function getTokenCount(prompt: string | AnthropicChatMessage[]) {
+export async function getTokenCount(
+  prompt: string | { system: string; messages: AnthropicChatMessage[] }
+) {
   if (typeof prompt !== "string") {
     return getTokenCountForMessages(prompt);
   }
@@ -34,9 +36,17 @@ export async function getTokenCount(prompt: string | AnthropicChatMessage[]) {
   };
 }
 
-async function getTokenCountForMessages(messages: AnthropicChatMessage[]) {
+async function getTokenCountForMessages({
+  system,
+  messages,
+}: {
+  system: string;
+  messages: AnthropicChatMessage[];
+}) {
   let numTokens = 0;
 
+  numTokens += (await getTokenCount(system)).token_count;
+
   for (const message of messages) {
     const { content, role } = message;
     numTokens += role === "user" ? userRoleCount : assistantRoleCount;
diff --git a/src/shared/tokenization/tokenizer.ts b/src/shared/tokenization/tokenizer.ts
index 8c86b33..1b03f3d 100644
--- a/src/shared/tokenization/tokenizer.ts
+++ b/src/shared/tokenization/tokenizer.ts
@@ -35,7 +35,7 @@ type OpenAIChatTokenCountRequest = {
 };
 
 type AnthropicChatTokenCountRequest = {
-  prompt: AnthropicChatMessage[];
+  prompt: { system: string; messages: AnthropicChatMessage[] };
   completion?: never;
   service: "anthropic-chat";
 };