diff --git a/packages/amazonq/.changes/next-release/Bug Fix-279c3a22-246e-41ca-9a42-3e446cdb9565.json b/packages/amazonq/.changes/next-release/Bug Fix-279c3a22-246e-41ca-9a42-3e446cdb9565.json
new file mode 100644
index 00000000000..28986810e43
--- /dev/null
+++ b/packages/amazonq/.changes/next-release/Bug Fix-279c3a22-246e-41ca-9a42-3e446cdb9565.json	
@@ -0,0 +1,4 @@
+{
+	"type": "Bug Fix",
+	"description": "Inline Suggestions: Occasional `ValidationException` if user context has too many characters."
+}
diff --git a/packages/core/src/codewhisperer/models/constants.ts b/packages/core/src/codewhisperer/models/constants.ts
index 846d9117066..92c51509a2f 100644
--- a/packages/core/src/codewhisperer/models/constants.ts
+++ b/packages/core/src/codewhisperer/models/constants.ts
@@ -712,6 +712,7 @@ export const crossFileContextConfig = {
     numberOfChunkToFetch: 60,
     topK: 3,
     numberOfLinesEachChunk: 50,
+    maximumTotalLength: 20480,
 }
 
 export const utgConfig = {
diff --git a/packages/core/src/codewhisperer/util/supplementalContext/crossFileContextUtil.ts b/packages/core/src/codewhisperer/util/supplementalContext/crossFileContextUtil.ts
index 1c4bd4637ba..1352f3ae8c8 100644
--- a/packages/core/src/codewhisperer/util/supplementalContext/crossFileContextUtil.ts
+++ b/packages/core/src/codewhisperer/util/supplementalContext/crossFileContextUtil.ts
@@ -132,9 +132,16 @@ export async function fetchSupplementalContextForSrcV1(
 
     // Step 4: Transform best chunks to supplemental contexts
     const supplementalContexts: CodeWhispererSupplementalContextItem[] = []
+    let totalLength = 0
     for (const chunk of bestChunks) {
         throwIfCancelled(cancellationToken)
 
+        totalLength += chunk.nextContent.length
+
+        if (totalLength > crossFileContextConfig.maximumTotalLength) {
+            break
+        }
+
         supplementalContexts.push({
             filePath: chunk.fileName,
             content: chunk.nextContent,