diff --git a/packages/core/src/tools/grep.ts b/packages/core/src/tools/grep.ts
index 6099b3c23c..6e6a73af96 100644
--- a/packages/core/src/tools/grep.ts
+++ b/packages/core/src/tools/grep.ts
@@ -311,7 +311,7 @@ class GrepToolInvocation extends BaseToolInvocation<
 
       llmContent += `:\n---\n`;
 
-      if (matchCount <= 3 && matchCount > 0 && !this.params.names_only) {
+      if (matchCount === 1 && matchCount > 0 && !this.params.names_only) {
         for (const filePath in matchesByFile) {
           const fileMatches = matchesByFile[filePath];
           let fileLines: string[] | null = null;
@@ -332,10 +332,10 @@ class GrepToolInvocation extends BaseToolInvocation<
 
           for (const match of fileMatches) {
             if (fileLines) {
-              const startLine = Math.max(0, match.lineNumber - 1 - 15);
+              const startLine = Math.max(0, match.lineNumber - 1 - 50);
               const endLine = Math.min(
                 fileLines.length,
-                match.lineNumber - 1 + 15 + 1,
+                match.lineNumber - 1 + 50 + 1,
               );
               const contextLines = fileLines.slice(startLine, endLine);
 
diff --git a/packages/core/src/tools/ripGrep.ts b/packages/core/src/tools/ripGrep.ts
index b991467ae0..aff76524df 100644
--- a/packages/core/src/tools/ripGrep.ts
+++ b/packages/core/src/tools/ripGrep.ts
@@ -313,7 +313,7 @@ class GrepToolInvocation extends BaseToolInvocation<
 
       // Greedy Grep: If match count is low and no context was requested, automatically return context.
       if (
-        matchCount <= 3 &&
+        matchCount === 1 &&
         matchCount > 0 &&
         !this.params.names_only &&
         !this.params.context &&
@@ -340,10 +340,10 @@ class GrepToolInvocation extends BaseToolInvocation<
             const newFileMatches: GrepMatch[] = [];
             const seenLines = new Set<number>();
             for (const match of fileMatches) {
-              const startLine = Math.max(0, match.lineNumber - 1 - 15);
+              const startLine = Math.max(0, match.lineNumber - 1 - 50);
               const endLine = Math.min(
                 fileLines.length,
-                match.lineNumber - 1 + 15 + 1,
+                match.lineNumber - 1 + 50 + 1,
               );
               for (let i = startLine; i < endLine; i++) {
                 if (!seenLines.has(i + 1)) {