diff --git a/apps/server/src/scheduledTasks/webhookTemplate.test.ts b/apps/server/src/scheduledTasks/webhookTemplate.test.ts
index 8b6f11e91f9f020bc3f9f7e3d38cd136899e54fb..f86a433c92e501d7e016b9f03f54355ac22a468c 100644
--- a/apps/server/src/scheduledTasks/webhookTemplate.test.ts
+++ b/apps/server/src/scheduledTasks/webhookTemplate.test.ts
@@ -52,6 +52,25 @@ describe("renderWebhookPrompt", () => {
     assert.deepEqual(rendered.missing, ["body.nope", "headers.x-missing", "unknown"]);
   });
 
+  it("trims placeholder whitespace before resolving and reporting missing fields", () => {
+    const rendered = renderWebhookPrompt(
+      "{{\tbody.action\n}}|{{  body.nope  }}|{{\nbody.nope\t}}|{{ \t\n }}",
+      githubPullRequest,
+    );
+    assert.equal(rendered.prompt, "opened|||");
+    assert.deepEqual(rendered.missing, ["body.nope", ""]);
+  });
+
+  it("preserves unclosed whitespace-heavy placeholders and resolves later valid ones", () => {
+    const unfinished = `Notify {{${" ".repeat(1024)}body`;
+    const rendered = renderWebhookPrompt(
+      `${unfinished}\n{{body.pull_request.number}}`,
+      githubPullRequest,
+    );
+    assert.equal(rendered.prompt, `${unfinished}\n45`);
+    assert.deepEqual(rendered.missing, []);
+  });
+
   it("addresses form-encoded bodies and leaves other bodies to {{body}}", () => {
     const form = renderWebhookPrompt("{{body.text}} by {{body.user_name}}", {
       ...githubPullRequest,
diff --git a/apps/server/src/scheduledTasks/webhookTemplate.ts b/apps/server/src/scheduledTasks/webhookTemplate.ts
index 74c0f08ae7781dab7fb4f886c897988bd53f1b30..a0540e4a1766a1ee36dbbb44e8cf34a60ac6ac96 100644
--- a/apps/server/src/scheduledTasks/webhookTemplate.ts
+++ b/apps/server/src/scheduledTasks/webhookTemplate.ts
@@ -69,7 +69,8 @@ export function redactQuery(query: string): string {
     .join("&");
 }
 
-const PLACEHOLDER = /\{\{\s*([^{}]*?)\s*\}\}/g;
+// Trim after matching so unclosed placeholders cannot backtrack over whitespace partitions.
+const PLACEHOLDER = /\{\{([^{}]*)\}\}/g;
 
 function parseBody(request: WebhookRequest): unknown {
   const contentType = (request.headers["content-type"] ?? "").toLowerCase();
@@ -144,7 +145,8 @@ export function renderWebhookPrompt(
     }
   };
 
-  const prompt = template.replace(PLACEHOLDER, (_match, expression: string) => {
+  const prompt = template.replace(PLACEHOLDER, (_match, rawExpression: string) => {
+    const expression = rawExpression.trim();
     const value = resolve(expression);
     if (value === undefined || value === null) {
       if (!missing.includes(expression)) missing.push(expression);