diff --git a/server.py b/server.py
index ecb857b..f090db4 100644
--- a/server.py
+++ b/server.py
@@ -52,6 +52,48 @@ def log_context_prefix() -> str:
     return ""
 
 
+# -------------------- DATE UTILS --------------------
+
+from email.utils import parsedate_to_datetime
+from datetime import datetime, timezone
+
+
+def parse_email_date(date_str: str) -> datetime:
+    """
+    Parse an email Date header into a timezone-aware datetime.
+    Fallback: treat as UTC if ambiguous.
+    """
+    if not date_str:
+        return datetime.min.replace(tzinfo=timezone.utc)
+    try:
+        dt = parsedate_to_datetime(date_str)
+        if dt.tzinfo is None:
+            dt = dt.replace(tzinfo=timezone.utc)
+        return dt
+    except Exception:
+        return datetime.min.replace(tzinfo=timezone.utc)
+
+
+def sort_by_date_oldest_first(items: list[dict], date_field: str = "date") -> list[dict]:
+    """
+    Sort items (e.g. emails or thread messages) by date, oldest first.
+    """
+    def key(item):
+        return parse_email_date(item.get(date_field, ""))
+    return sorted(items, key=key)
+
+
+def normalize_date(date_str: str) -> str:
+    """
+    Convert an email Date header to a clear ISO 8601 UTC string.
+    Returns original if parsing fails.
+    """
+    dt = parse_email_date(date_str)
+    if dt == datetime.min:
+        return date_str or ""
+    return dt.astimezone(timezone.utc).strftime("%Y-%m-%dT%H:%M:%SZ")
+
+
 # -------------------- LOGGING (Docker-friendly) --------------------
 
 log_level = os.getenv("LOG_LEVEL", "INFO").upper()
@@ -1212,7 +1254,7 @@ TOOLS = [
     },
     {
         "name": "list_unread_emails",
-        "description": "List unread emails with minimal content to save context. Use this first when triaging many emails, then use get_email or summarize_email on selected messages.",
+        "description": "List unread emails with minimal content to save context. Use this first when triaging many emails, then use get_email or summarize_email on selected messages. Returns results sorted oldest → newest with ISO 8601 dates.",
         "inputSchema": {
             "type": "object",
             "properties": {
@@ -1227,7 +1269,7 @@ TOOLS = [
     },
     {
         "name": "get_email",
-        "description": "Fetch the full content of a single email by UID. Use this after scanning with list_unread_emails or get_unread_summary for emails you need to read in detail.",
+        "description": "Fetch the full content of a single email by UID. Use this after scanning with list_unread_emails or get_unread_summary for emails you need to read in detail. Date is returned in ISO 8601 format.",
         "inputSchema": {
             "type": "object",
             "properties": {
@@ -1241,7 +1283,7 @@ TOOLS = [
     },
     {
         "name": "summarize_email",
-        "description": "Summarize a single email using an external model (if configured) to reduce context usage. Use this when you need to understand an email quickly without loading its full text.",
+        "description": "Summarize a single email using an external model (if configured) to reduce context usage. Use this when you need to understand an email quickly without loading its full text. Date is returned in ISO 8601 format.",
         "inputSchema": {
             "type": "object",
             "properties": {
@@ -1255,7 +1297,7 @@ TOOLS = [
     },
     {
         "name": "get_thread",
-        "description": "Get a concise view of the conversation thread for a given email. Use this to understand context without loading all message bodies.",
+        "description": "Get a concise view of the conversation thread for a given email. Use this to understand context without loading all message bodies. Messages are returned sorted oldest → newest with ISO 8601 dates.",
         "inputSchema": {
             "type": "object",
             "properties": {
@@ -1715,6 +1757,10 @@ def search_messages_impl(account=None, folder="INBOX", query="", since=None, max
     try:
         login_imap(imap, acc)
         results = search_messages(imap, folder=folder, query=query, since=since, max_results=max_results)
+        # Normalize dates and sort oldest → newest
+        for m in results:
+            m["date"] = normalize_date(m.get("date", ""))
+        results = sort_by_date_oldest_first(results)
         return {"messages": results}
     finally:
         imap.logout()
@@ -1847,9 +1893,11 @@ def get_unread_summary_impl(account=None, folder="INBOX"):
                 "uid": uid,
                 "subject": msg["subject"],
                 "from": msg["from"],
-                "date": msg["date"],
-                "snippet": (msg["body_plain"] or "")[:300],
+                "date": normalize_date(msg["date"]),
+                "snippet": (msg["body_plain"] or "")[:250].strip(),
             })
+        # Sort oldest → newest
+        previews = sort_by_date_oldest_first(previews)
         return {
             "folder": folder,
             "unread_count": count,
@@ -1862,6 +1910,7 @@ def get_unread_summary_impl(account=None, folder="INBOX"):
 def list_unread_emails_impl(account=None, folder="INBOX", max_results=50, include_body=False, since=None):
     """
     Metadata-only (or limited) listing of unread emails to reduce context usage.
+    Returns results sorted oldest → newest by date.
     """
     acc = get_account(account)
     imap = create_imap(acc)
@@ -1881,8 +1930,9 @@ def list_unread_emails_impl(account=None, folder="INBOX", max_results=50, includ
             ids = data[0].split()
 
         uids = [int(u) for u in ids]
-        count = len(uids)
-        uids = uids[-max_results:]  # take most recent
+        total_unread = len(uids)
+        # take most recent, then sort chronologically
+        uids = uids[-max_results:]
 
         emails = []
         for uid in uids:
@@ -1891,7 +1941,7 @@ def list_unread_emails_impl(account=None, folder="INBOX", max_results=50, includ
             except Exception:
                 continue
 
-            snippet = (msg["body_plain"] or "")[:300].strip()
+            snippet = (msg["body_plain"] or "")[:250].strip()
             att_info = list_attachments_for_uid(imap, folder, uid)
             has_attachments = len(att_info) > 0
 
@@ -1899,9 +1949,7 @@ def list_unread_emails_impl(account=None, folder="INBOX", max_results=50, includ
                 "uid": uid,
                 "subject": msg["subject"],
                 "from": msg["from"],
-                "to": msg["to"],
-                "date": msg["date"],
-                "flags": msg["flags"],
+                "date": normalize_date(msg["date"]),
                 "snippet": snippet,
                 "has_attachments": has_attachments,
             }
@@ -1912,9 +1960,12 @@ def list_unread_emails_impl(account=None, folder="INBOX", max_results=50, includ
 
             emails.append(item)
 
+        # Sort oldest → newest by date
+        emails = sort_by_date_oldest_first(emails)
+
         return {
             "folder": folder,
-            "total_unread": count,
+            "total_unread": total_unread,
             "returned": len(emails),
             "emails": emails,
         }
@@ -1925,6 +1976,7 @@ def list_unread_emails_impl(account=None, folder="INBOX", max_results=50, includ
 def get_email_impl(account=None, folder="INBOX", uid=None, include_html=False):
     """
     Fetch the full content of a single email by UID.
+    Returns a normalized ISO 8601 date for reliable parsing.
     """
     acc = get_account(account)
     imap = create_imap(acc)
@@ -1939,7 +1991,7 @@ def get_email_impl(account=None, folder="INBOX", uid=None, include_html=False):
             "from": msg["from"],
             "to": msg["to"],
             "cc": msg["cc"],
-            "date": msg["date"],
+            "date": normalize_date(msg["date"]),
             "body_plain": msg["body_plain"],
             "attachments": att_info,
         }
@@ -1956,6 +2008,7 @@ def summarize_email_impl(account=None, folder="INBOX", uid=None, max_length=150)
     """
     Use an external model to summarize a single email.
     Falls back to a short plain-text prefix if external model is unavailable.
+    Returns a normalized ISO 8601 date for reliable parsing.
     """
     acc = get_account(account)
     imap = create_imap(acc)
@@ -1972,7 +2025,7 @@ def summarize_email_impl(account=None, folder="INBOX", uid=None, max_length=150)
             "uid": uid,
             "subject": msg["subject"],
             "from": msg["from"],
-            "date": msg["date"],
+            "date": normalize_date(msg["date"]),
             "summary": "(No readable content)"
         }
 
@@ -1992,7 +2045,7 @@ def summarize_email_impl(account=None, folder="INBOX", uid=None, max_length=150)
         "uid": uid,
         "subject": msg["subject"],
         "from": msg["from"],
-        "date": msg["date"],
+        "date": normalize_date(msg["date"]),
         "summary": summary + attachments_note,
     }
 
@@ -2000,6 +2053,7 @@ def summarize_email_impl(account=None, folder="INBOX", uid=None, max_length=150)
 def get_thread_impl(account=None, folder="INBOX", uid=None, max_messages=10):
     """
     Return a concise thread view for a given message UID.
+    Messages are returned sorted oldest → newest with normalized dates.
     """
     acc = get_account(account)
     imap = create_imap(acc)
@@ -2067,11 +2121,14 @@ def get_thread_impl(account=None, folder="INBOX", uid=None, max_messages=10):
             messages.append({
                 "uid": u,
                 "from": msg["from"],
-                "date": msg["date"],
+                "date": normalize_date(msg["date"]),
                 "subject": msg["subject"],
                 "snippet": snippet,
             })
 
+        # Sort oldest → newest
+        messages = sort_by_date_oldest_first(messages)
+
         return {
             "subject": subject,
             "participants": list(participants),