diff --git a/src/worker.ts b/src/worker.ts
index fc546ce..5bf7e12 100644
--- a/src/worker.ts
+++ b/src/worker.ts
@@ -697,7 +697,16 @@ const plugin = definePlugin({
 					const matched = commentId
 						? comments.find((c) => c.id === commentId)
 						: undefined;
-					const latest = comments[comments.length - 1];
+					// Newest by createdAt — do NOT rely on listComments array order.
+					const latest = comments.reduce<(typeof comments)[number] | null>(
+						(acc, c) =>
+							!acc ||
+							new Date(c.createdAt).getTime() >
+								new Date(acc.createdAt).getTime()
+								? c
+								: acc,
+						null,
+					);
 					commentBody =
 						matched?.body ||
 						latest?.body ||
@@ -997,14 +1006,28 @@ const plugin = definePlugin({
 						);
 						if (comments.length === 0) continue;
 
-						// "Pending" = the conversation's last word is the chair's, with
-						// no agent reply after it. listComments is chronological (newest
-						// last). If an agent already responded, the comment was handled —
-						// skip. This both targets the exact failure (chair commented, no
-						// agent response) and avoids re-routing historically-answered
-						// comments on first run after deploy.
-						const last = comments[comments.length - 1];
-						if (last.authorType !== "user") continue;
+						// "Pending" = the chair spoke last among real participants: the
+						// newest USER comment is newer than the newest AGENT comment (or
+						// no agent has commented yet), so an agent never responded to it.
+						// Order-independent (sort by createdAt, do NOT rely on the array
+						// order of listComments) and system comments are ignored — an
+						// automated "draft ready" line is not an agent response. This
+						// targets the exact failure (chair commented, no agent reply) and
+						// skips historically-answered comments.
+						const ts = (c: { createdAt: string | Date }) =>
+							new Date(c.createdAt).getTime();
+						let newestUser: (typeof comments)[number] | null = null;
+						let newestAgent: (typeof comments)[number] | null = null;
+						for (const c of comments) {
+							if (c.authorType === "user") {
+								if (!newestUser || ts(c) > ts(newestUser)) newestUser = c;
+							} else if (c.authorType === "agent") {
+								if (!newestAgent || ts(c) > ts(newestAgent)) newestAgent = c;
+							}
+						}
+						if (!newestUser) continue; // no chair comment
+						// An agent has already responded after the chair — handled.
+						if (newestAgent && ts(newestAgent) >= ts(newestUser)) continue;
 
 						const marker = await ctx.state.get({
 							scopeKind: "issue",
@@ -1012,18 +1035,18 @@ const plugin = definePlugin({
 							stateKey: LAST_ROUTED_COMMENT_KEY,
 						});
 						// Already routed (CEO may still be working) — don't re-fire.
-						if (marker === last.id) continue;
+						if (marker === newestUser.id) continue;
 
 						ctx.logger.info(
 							"route-pending-comments: re-routing unrouted user comment",
-							{ issueId: issue.id, commentId: last.id },
+							{ issueId: issue.id, commentId: newestUser.id },
 						);
 						await routeCommentToCeo({
 							issue,
 							companyId: company.id,
 							ceoAgentId,
-							commentBody: last.body,
-							commentId: last.id,
+							commentBody: newestUser.body,
+							commentId: newestUser.id,
 							source: "sweep",
 						});
 					} catch (err) {