diff --git a/package.json b/package.json
index 60139c7..9f6d533 100644
--- a/package.json
+++ b/package.json
@@ -2,7 +2,7 @@
   "name": "claude-dev",
   "displayName": "Claude Dev",
   "description": "Autonomous coding agent right in your IDE, capable of creating/editing files, executing commands, and more with your permission every step of the way.",
-  "version": "1.5.2",
+  "version": "1.5.3",
   "icon": "icon.png",
   "engines": {
     "vscode": "^1.84.0"
diff --git a/src/utils/context-management.ts b/src/utils/context-management.ts
index 6fc817e..f2442b1 100644
--- a/src/utils/context-management.ts
+++ b/src/utils/context-management.ts
@@ -9,7 +9,7 @@ export function isWithinContextWindow(
 	tools: Anthropic.Messages.Tool[],
 	messages: Anthropic.Messages.MessageParam[]
 ): boolean {
-	const adjustedContextWindow = contextWindow - 10_000 // Buffer to account for tokenizer differences
+	const adjustedContextWindow = contextWindow * 0.75 // Buffer to account for tokenizer differences
 	// counting tokens is expensive, so we first try to estimate before doing a more accurate calculation
 	const estimatedTotalMessageTokens = countTokens(systemPrompt + JSON.stringify(tools) + JSON.stringify(messages))
 	if (estimatedTotalMessageTokens <= adjustedContextWindow) {