docs(progress): I-G-Rest Split Schritt 4 — smtp_send extrahiert, mail/services.py -56%

refactor(i-g): BUG-018 Pilot Split Schritt 4 — smtp_send extrahiert (~320 Z.)
SMTP Send Block (F-MAIL-02) aus services.py extrahiert: send_mail_via_smtp/reply_to_mail/forward_mail nach smtp_send.py (321 Z.). services.py jetzt ~1365 Z. (von 3087). Fix waehrend Extraktion: aiosmtplib bleibt als Modulattribut in services.py mit noqa F401 — test_mail.py patcht services.aiosmtplib.SMTP und braucht das Attribut. Beweis: mail+sig_label_routes 51/51 passed in 107.28s; ruff clean.
2026-08-26 13:16:14 +02:00 · 2026-08-26 13:06:46 +02:00
3 changed files with 365 additions and 324 deletions
@@ -119,7 +119,7 @@
 | I-G-1 | BUG-022/070 Audits: npm audit = 0 vulnerabilities bereits sauber; pip-audit fand **9 known CVEs in starlette 0.46.2** (PYSEC-2026-161/248/249/1941/1942/2280/2281) — Dilemma: fastapi 0.115.x pinnt starlette<0.47.0, Fixes brauchen >=1.x | ✅ **0 pip findings**: fastapi 0.141.1 (zieht starlette ohne Obergrenze) + starlette direkt auf 1.3.1 gepinnt in requirements.txt; Regressionssmoke auth+api_audit 19/19 + mail+permissions+outbox+audit_middleware+cross_tenant_v2 84/85 (1 Failure = bekannter Reihenfolge-Vorbestand, isolat grün) | 34c9c85 |
 | I-G-2 | i18n ×258 hardcoded Strings gemessen (Top-Hotspot AISettings.tsx mit 32): Provider-Eigennamen bewusst belassen, ~20 echte UI-Strings | ✅ Exemplarischer Durchstich: useTranslation-Hooks in alle 4 Tab-Komponenten, aiSettings.*-Namespace in de+en ergänzt; tsc=0; AISettings-Tests 18/18; Rest folgt im selben Muster | e7afbaa |
 | I-G-3 | i18n Hotspot Nr.2: ProactiveAISettings.tsx (15+ deutsche Hardcodes inkl. title/toggle/categories/confidence/rateLimit/model/heartbeat/targetRoom + categoryLabels auf t()-Keys) | ✅ **10/10 Tests grün**, tsc=0; proactiveAI.*-Namespace in de+en; categoryLabels-Record durch t()-basierte categoryKeys ersetzt; modelOptions inline mit t()-Labels | 26b5ae9 |
-| I-G-Rest | God Objects: 35 Python-Dateien >500 Z. — Plan verlangt Hotspot-priorisierte Splits mit eigenem Commit je Datei, NICHT Big-Bang | 🟡 **Pilot läuft**: mail/services.py 3087→~1680 Z. (**−46%**) in 3 Schritten: S1 = crypto+sanitize+pgp (pure functions), S2 = serializers+text_utils (inkl. NEVER-password-Contract), S3 = imap_sync.py (~1070 Z.: folder/account sync, thread-id, German folder names, quota parser) + attachments.py (path-traversal-geschützt) + get_account_password als async (Fix während Extraktion — erste Version war sync und brach send/reply/forward_mail). Re-Export via noqa F401 überall; Beweise: mail+sig_label_routes **51/51 grün** nach jedem Schritt; ruff clean | a1d5e56, be81fe5, 6702d69 |
+| I-G-Rest | God Objects: 35 Python-Dateien >500 Z. — Plan verlangt Hotspot-priorisierte Splits mit eigenem Commit je Datei, NICHT Big-Bang | 🟡 **Pilot läuft**: mail/services.py 3087→~1365 Z. (**−56%**) in 4 Schritten: S1 = crypto+sanitize+pgp (pure functions), S2 = serializers+text_utils (NEVER-password-Contract), S3 = imap_sync.py (~1070 Z.) + attachments.py (path-traversal-geschützt) + get_account_password async-Fix, S4 = smtp_send.py (~320 Z.: send/reply/forward) — inkl. aiosmtplib-Modulattribut-Fix für Test-Mocks (services.aiosmtplib.SMTP). Re-Export via noqa F401 überall; Beweise: mail+sig_label_routes **51/51 grün** nach jedem Schritt; ruff clean | a1d5e56, be81fe5, 6702d69, fce17aa |
 | G2 | Session-Revocation bei Passwortänderung — Befund differenzierter als Plan annahm: Reset-via-Token (confirm_password_reset) revocierte Sessions bereits korrekt (Redis scan_iter session:*), aber Profil-/Admin-Pfad (users.py PATCH → update_user mit new_password) liess alle anderen Sessions aktiv — Angreifer mit gestohlener Session blieb aktiv | ✅ **120/120 grün** (auth+user_service+rbac_comprehensive in 144s); revoke_user_redis_sessions(user_id)-Helper in auth.py extrahiert (never-raises), von beiden Pfaden genutzt; Postgres sessions-Tabelle unberührt (Audit-Trail by Design) | 0baec27 |
 | G1-a | DSGVO Art. 17 Löschung **nicht funktionsfähig**: POST /dsar/{user_id} queued einen process_dsar-Job der nirgends implementiert war (grep: nur die Route referenziert ihn) — DSAR-Requests verschwanden im Nirvana; Art. 15 Auskunft lieferte nur 3 statt aller versprochenen Kategorien | ✅ **4/4 grün** (test_g1_dsar): _dsar_collect_user_data sammelt profile+contacts+audit_log+notifications (Art. 15/20); _dsar_execute_deletion führt Art. 17 aus — contacts soft-delete (Audit-/Aufbewahrungspflichten respektiert), notifications hard-delete, User anonymisiert + deaktiviert mit FK-Integrität für Audit-Zeilen, dsar_erasure-Audit-Eintrag; process_dsar dispatcht access/deletion/rectification (rectification = manuelle Bearbeitung via Systemnachricht) | f4a5937 |
 | G1-b | dsgvo-export-Endpoint-Docstring versprach Mail-Accounts/Tasks/Calendar/Comm-Messages — geliefert wurden nie welche (Docstring-Fiktion) | ⏳ Export erweitern auf die fehlenden Kategorien als Follow-up (Job-Helfer _dsar_collect_user_data ist der Erweiterungspunkt); Kernpflichten Art. 15/17 sind jetzt funktionsfähig | — |
@@ -13,7 +13,7 @@ from email.utils import formataddr, formatdate, make_msgid

 import aiofiles
 import aioimaplib
-import aiosmtplib
+import aiosmtplib  # noqa: F401 — test_mail.py patches services.aiosmtplib.SMTP
 from sqlalchemy import and_, or_, select
 from sqlalchemy.ext.asyncio import AsyncSession

@@ -43,7 +43,6 @@ from app.plugins.builtins.mail.models import (
    MailFolder,
    MailLabelAssignment,
    MailRule,
-    MailSignature,
    VacationSentLog,
 )
 from app.plugins.builtins.mail.pgp import (  # noqa: E402,F401
@@ -63,6 +62,11 @@ from app.plugins.builtins.mail.serializers import (  # noqa: E402,F401
    signature_to_response,
    template_to_response,
 )
+from app.plugins.builtins.mail.smtp_send import (  # noqa: E402,F401
+    forward_mail,
+    reply_to_mail,
+    send_mail_via_smtp,
+)
 from app.plugins.builtins.mail.text_utils import (  # noqa: E402,F401
    _strip_html,
    extract_email_addresses,
@@ -242,327 +246,6 @@ async def update_mail_account(db: AsyncSession, account: MailAccount, data: dict
    return account


-# ─── SMTP Send Service (F-MAIL-02) ───
-
-
-async def send_mail_via_smtp(
-    db: AsyncSession,
-    *,
-    tenant_id: uuid.UUID,
-    user_id: uuid.UUID,
-    account: MailAccount,
-    to_addrs: list[str],
-    cc_addrs: list[str] = None,
-    bcc_addrs: list[str] = None,
-    subject: str = "",
-    body_html: str = "",
-    body_text: str = "",
-    in_reply_to: str | None = None,
-    references_header: str | None = None,
-    signature: MailSignature | None = None,
-    attachment_paths: list[dict] | None = None,
-) -> dict:
-    """Send an email via SMTP using aiosmtplib.
-
-    Args:
-        attachment_paths: list of dicts with keys 'path', 'filename', 'mime_type'
-                          pointing to files on disk to attach.
-    """
-    cc_addrs = cc_addrs or []
-    bcc_addrs = bcc_addrs or []
-    attachment_paths = attachment_paths or []
-    logger = logging.getLogger(__name__)
-
-    # Apply signature if provided
-    if signature and signature.body_html:
-        body_html = body_html + f"<br><br>{signature.body_html}"
-        if body_text:
-            body_text = body_text + "\n\n-- \n" + _strip_html(signature.body_html)
-
-    # Build email message
-    msg = EmailMessage()
-    msg["From"] = formataddr((account.display_name or "", account.email_address))
-    msg["To"] = ", ".join(to_addrs)
-    if cc_addrs:
-        msg["Cc"] = ", ".join(cc_addrs)
-    msg["Subject"] = subject
-    msg["Date"] = formatdate(localtime=True)
-    msg_id = make_msgid(
-        domain=account.email_address.split("@")[-1] if "@" in account.email_address else "localhost"
-    )
-    msg["Message-ID"] = msg_id
-    if in_reply_to:
-        msg["In-Reply-To"] = in_reply_to
-    if references_header:
-        msg["References"] = references_header
-
-    if body_html:
-        msg.set_content(body_text or _strip_html(body_html), subtype="plain")
-        msg.add_alternative(body_html, subtype="html")
-    else:
-        msg.set_content(body_text, subtype="plain")
-
-    # Add attachments to the message
-    for att_info in attachment_paths:
-        file_path = att_info.get("path", "")
-        filename = att_info.get("filename", os.path.basename(file_path))
-        mime_type = att_info.get("mime_type", "application/octet-stream")
-        if not file_path or not os.path.exists(file_path):  # noqa: ASYNC240
-            continue
-        async with aiofiles.open(file_path, "rb") as f:
-            content = await f.read()
-        # Determine maintype/subtype from mime_type
-        if "/" in mime_type:
-            maintype, subtype = mime_type.split("/", 1)
-        else:
-            maintype, subtype = "application", "octet-stream"
-        msg.add_attachment(
-            content,
-            maintype=maintype,
-            subtype=subtype,
-            filename=filename,
-        )
-
-    # ── Hook: mail.before_send (Filter) ──
-    from app.core.hooks import apply_filters
-    mail_data = {
-        "subject": subject,
-        "body_html": body_html,
-        "body_text": body_text,
-        "to_addrs": to_addrs,
-        "cc_addrs": cc_addrs,
-        "bcc_addrs": bcc_addrs,
-        "attachment_paths": attachment_paths,
-    }
-    mail_data = await apply_filters("mail.before_send", mail_data)
-
-    # Send via SMTP
-    password = await get_account_password(account)
-    try:
-        smtp = aiosmtplib.SMTP(
-            hostname=account.smtp_host,
-            port=account.smtp_port,
-            use_tls=account.smtp_tls,
-        )
-        await smtp.connect()
-        await smtp.login(account.username, password)
-        recipients = to_addrs + cc_addrs + bcc_addrs
-        await smtp.send_message(msg, recipients=recipients)
-        await smtp.quit()
-
-        # ── Hook: mail.after_send (Action) ──
-        from app.core.hooks import do_action
-        await do_action("mail.after_send", mail_data, db=db, account=account, msg_id=msg_id)
-        await do_action("mail.after_update", mail_data, db=db, tenant_id=str(mail_data.get('tenant_id', '')) if isinstance(mail_data, dict) else None)
-
-        # Store sent mail in Sent folder — use configured mapping if set,
-        # otherwise flexible lookup to handle different IMAP naming conventions
-        if account.sent_folder_imap_name:
-            sent_folder = (
-                await db.execute(
-                    select(MailFolder).where(
-                        and_(
-                            MailFolder.account_id == account.id,
-                            MailFolder.imap_name == account.sent_folder_imap_name,
-                        )
-                    )
-                )
-            ).scalar_one_or_none()
-        else:
-            sent_folder = (
-                await db.execute(
-                    select(MailFolder).where(
-                        and_(
-                            MailFolder.account_id == account.id,
-                            MailFolder.imap_name.in_(
-                                ["Sent", "INBOX.Sent", "Sent Items", "Sent Mail"]
-                            ),
-                        )
-                    )
-                )
-            ).scalar_one_or_none()
-
-            if not sent_folder:
-                sent_folder = (
-                    await db.execute(
-                        select(MailFolder).where(
-                            and_(
-                                MailFolder.account_id == account.id,
-                                MailFolder.is_standard.is_(True),
-                                MailFolder.imap_name.ilike("%sent%"),
-                            )
-                        )
-                    )
-                ).scalar_one_or_none()
-
-        if sent_folder:
-            thread_id = _compute_thread_id(msg_id, references_header or "", in_reply_to)
-            sent_mail = Mail(
-                tenant_id=tenant_id,
-                account_id=account.id,
-                folder_id=sent_folder.id,
-                message_id=msg_id,
-                thread_id=thread_id,
-                in_reply_to=in_reply_to,
-                references_header=references_header,
-                subject=subject,
-                from_address=account.email_address,
-                to_addresses=", ".join(to_addrs),
-                cc_addresses=", ".join(cc_addrs),
-                bcc_addresses=", ".join(bcc_addrs),
-                body_text=body_text or _strip_html(body_html),
-                body_html=body_html,
-                body_html_sanitized=sanitize_html(body_html),
-                is_seen=True,
-                is_answered=bool(in_reply_to),
-                sent_at=datetime.now(UTC),
-            )
-            db.add(sent_mail)
-            await db.flush()
-
-            # Upload sent mail to IMAP Sent folder via APPEND
-            try:
-                imap_client = aioimaplib.IMAP4_SSL(host=account.imap_host, port=account.imap_port)
-                await imap_client.wait_hello_from_server()
-                await imap_client.login(account.username, password)
-                # Build raw email bytes for APPEND
-                raw_email_bytes = msg.as_bytes()
-                append_resp = await imap_client.append(
-                    sent_folder.imap_name,
-                    r'(\Seen)',
-                    None,
-                    raw_email_bytes,
-                )
-                if append_resp.result == 'OK':
-                    logger.info("send_mail: uploaded sent mail to IMAP folder %s", sent_folder.imap_name)
-                    # Retrieve the new UID for the appended mail by searching for its Message-ID
-                    try:
-                        await imap_client.select(sent_folder.imap_name)
-                        search_resp = await imap_client.uid_search(f'HEADER Message-ID "{msg_id}"')
-                        uid_raw = search_resp[1][0] if search_resp[1] and search_resp[1][0] else b''
-                        if isinstance(uid_raw, (bytes, bytearray)) and uid_raw:
-                            new_uids = uid_raw.decode().split()
-                            if new_uids:
-                                sent_mail.imap_uid = new_uids[0]
-                                logger.info("send_mail: set imap_uid=%s for sent mail %s", new_uids[0], sent_mail.id)
-                    except Exception as uid_exc:
-                        logger.warning("send_mail: could not retrieve UID after APPEND: %s", uid_exc)
-                else:
-                    logger.warning("send_mail: IMAP APPEND failed for sent folder %s: %s", sent_folder.imap_name, append_resp)
-                await imap_client.logout()
-            except Exception as imap_exc:
-                logger.warning("send_mail: IMAP APPEND failed (non-critical): %s", imap_exc)
-
-        # ── Notification: mail sent ──
-        try:
-            await create_notification(
-                db, tenant_id, user_id,
-                "mail_sent",
-                "E-Mail gesendet",
-                subject,
-            )
-            await db.flush()
-        except Exception:
-            logger.debug("Ignored exception in mail service", exc_info=True)
-
-        return {"status": "sent", "message_id": msg_id}
-    except Exception as e:
-        # ── Notification: send error ──
-        try:
-            await create_notification(
-                db, tenant_id, user_id,
-                "mail_send_error",
-                "E-Mail konnte nicht gesendet werden",
-                str(e),
-            )
-            await db.flush()
-        except Exception:
-            logger.debug("Ignored exception in mail service", exc_info=True)
-        return {"status": "error", "error": str(e)}
-
-
-async def reply_to_mail(
-    db: AsyncSession,
-    *,
-    tenant_id: uuid.UUID,
-    user_id: uuid.UUID,
-    original_mail: Mail,
-    account: MailAccount,
-    body_html: str,
-    body_text: str = "",
-    reply_to_all: bool = False,
-    signature: MailSignature | None = None,
-) -> dict:
-    """Reply to a mail, setting In-Reply-To and References headers (F-MAIL-02)."""
-    to_addrs = [original_mail.from_address]
-    if reply_to_all and original_mail.cc_addresses:
-        to_addrs.extend([a.strip() for a in original_mail.cc_addresses.split(",") if a.strip()])
-
-    refs = original_mail.references_header or ""
-    new_refs = f"{refs} {original_mail.message_id}".strip()
-
-    result = await send_mail_via_smtp(
-        db,
-        tenant_id=tenant_id,
-        user_id=user_id,
-        account=account,
-        to_addrs=to_addrs,
-        subject=f"Re: {original_mail.subject}".replace("Re: Re: ", "Re: "),
-        body_html=body_html,
-        body_text=body_text,
-        in_reply_to=original_mail.message_id,
-        references_header=new_refs,
-        signature=signature,
-    )
-
-    # Mark original as answered
-    original_mail.is_answered = True
-    await db.flush()
-    return result
-
-
-async def forward_mail(
-    db: AsyncSession,
-    *,
-    tenant_id: uuid.UUID,
-    user_id: uuid.UUID,
-    original_mail: Mail,
-    account: MailAccount,
-    to_addrs: list[str],
-    cc_addrs: list[str] = None,
-    body_html: str = "",
-    body_text: str = "",
-    signature: MailSignature | None = None,
-) -> dict:
-    """Forward a mail with original as forwarded content (F-MAIL-02)."""
-    fwd_subject = f"Fwd: {original_mail.subject}".replace("Fwd: Fwd: ", "Fwd: ")
-    fwd_body = (
-        f"<br><br>----- Original Message -----<br>"
-        f"From: {original_mail.from_address}<br>"
-        f"Subject: {original_mail.subject}<br><br>"
-        f"{original_mail.body_html or original_mail.body_text}"
-    )
-    full_html = body_html + fwd_body
-    full_text = (body_text or _strip_html(body_html)) + "\n\n----- Original Message -----\n"
-
-    result = await send_mail_via_smtp(
-        db,
-        tenant_id=tenant_id,
-        user_id=user_id,
-        account=account,
-        to_addrs=to_addrs,
-        cc_addrs=cc_addrs or [],
-        subject=fwd_subject,
-        body_html=full_html,
-        body_text=full_text,
-        signature=signature,
-    )
-
-    original_mail.is_forwarded = True
-    await db.flush()
-    return result
-
-
 # ─── Template Service (F-MAIL-06) ───


@@ -0,0 +1,358 @@
+"""SMTP send service for the Mail plugin (F-MAIL-02).
+
+Extracted from services.py as part of the God-object split (BUG-018 pilot).
+Re-exported by ``app.plugins.builtins.mail.services``.
+
+Contains send_mail_via_smtp, reply_to_mail and forward_mail.
+"""
+
+from __future__ import annotations
+
+import logging
+import os
+import uuid
+from datetime import UTC, datetime
+from email.message import EmailMessage
+from email.utils import formataddr, formatdate, make_msgid
+
+import aiofiles
+import aioimaplib
+import aiosmtplib
+from sqlalchemy import and_, select
+from sqlalchemy.ext.asyncio import AsyncSession
+
+from app.core.notifications import create_notification
+from app.plugins.builtins.mail.imap_sync import (
+    _compute_thread_id,
+    get_account_password,
+)
+from app.plugins.builtins.mail.models import (
+    Mail,
+    MailAccount,
+    MailFolder,
+    MailSignature,
+)
+from app.plugins.builtins.mail.sanitize import sanitize_html
+from app.plugins.builtins.mail.text_utils import _strip_html
+
+logger = logging.getLogger(__name__)
+
+
+async def send_mail_via_smtp(
+    db: AsyncSession,
+    *,
+    tenant_id: uuid.UUID,
+    user_id: uuid.UUID,
+    account: MailAccount,
+    to_addrs: list[str],
+    cc_addrs: list[str] = None,
+    bcc_addrs: list[str] = None,
+    subject: str = "",
+    body_html: str = "",
+    body_text: str = "",
+    in_reply_to: str | None = None,
+    references_header: str | None = None,
+    signature: MailSignature | None = None,
+    attachment_paths: list[dict] | None = None,
+) -> dict:
+    """Send an email via SMTP using aiosmtplib.
+
+    Args:
+        attachment_paths: list of dicts with keys 'path', 'filename', 'mime_type'
+                          pointing to files on disk to attach.
+    """
+    cc_addrs = cc_addrs or []
+    bcc_addrs = bcc_addrs or []
+    attachment_paths = attachment_paths or []
+    logger = logging.getLogger(__name__)
+
+    # Apply signature if provided
+    if signature and signature.body_html:
+        body_html = body_html + f"<br><br>{signature.body_html}"
+        if body_text:
+            body_text = body_text + "\n\n-- \n" + _strip_html(signature.body_html)
+
+    # Build email message
+    msg = EmailMessage()
+    msg["From"] = formataddr((account.display_name or "", account.email_address))
+    msg["To"] = ", ".join(to_addrs)
+    if cc_addrs:
+        msg["Cc"] = ", ".join(cc_addrs)
+    msg["Subject"] = subject
+    msg["Date"] = formatdate(localtime=True)
+    msg_id = make_msgid(
+        domain=account.email_address.split("@")[-1] if "@" in account.email_address else "localhost"
+    )
+    msg["Message-ID"] = msg_id
+    if in_reply_to:
+        msg["In-Reply-To"] = in_reply_to
+    if references_header:
+        msg["References"] = references_header
+
+    if body_html:
+        msg.set_content(body_text or _strip_html(body_html), subtype="plain")
+        msg.add_alternative(body_html, subtype="html")
+    else:
+        msg.set_content(body_text, subtype="plain")
+
+    # Add attachments to the message
+    for att_info in attachment_paths:
+        file_path = att_info.get("path", "")
+        filename = att_info.get("filename", os.path.basename(file_path))
+        mime_type = att_info.get("mime_type", "application/octet-stream")
+        if not file_path or not os.path.exists(file_path):  # noqa: ASYNC240
+            continue
+        async with aiofiles.open(file_path, "rb") as f:
+            content = await f.read()
+        # Determine maintype/subtype from mime_type
+        if "/" in mime_type:
+            maintype, subtype = mime_type.split("/", 1)
+        else:
+            maintype, subtype = "application", "octet-stream"
+        msg.add_attachment(
+            content,
+            maintype=maintype,
+            subtype=subtype,
+            filename=filename,
+        )
+
+    # ── Hook: mail.before_send (Filter) ──
+    from app.core.hooks import apply_filters
+    mail_data = {
+        "subject": subject,
+        "body_html": body_html,
+        "body_text": body_text,
+        "to_addrs": to_addrs,
+        "cc_addrs": cc_addrs,
+        "bcc_addrs": bcc_addrs,
+        "attachment_paths": attachment_paths,
+    }
+    mail_data = await apply_filters("mail.before_send", mail_data)
+
+    # Send via SMTP
+    password = await get_account_password(account)
+    try:
+        smtp = aiosmtplib.SMTP(
+            hostname=account.smtp_host,
+            port=account.smtp_port,
+            use_tls=account.smtp_tls,
+        )
+        await smtp.connect()
+        await smtp.login(account.username, password)
+        recipients = to_addrs + cc_addrs + bcc_addrs
+        await smtp.send_message(msg, recipients=recipients)
+        await smtp.quit()
+
+        # ── Hook: mail.after_send (Action) ──
+        from app.core.hooks import do_action
+        await do_action("mail.after_send", mail_data, db=db, account=account, msg_id=msg_id)
+        await do_action("mail.after_update", mail_data, db=db, tenant_id=str(mail_data.get('tenant_id', '')) if isinstance(mail_data, dict) else None)
+
+        # Store sent mail in Sent folder — use configured mapping if set,
+        # otherwise flexible lookup to handle different IMAP naming conventions
+        if account.sent_folder_imap_name:
+            sent_folder = (
+                await db.execute(
+                    select(MailFolder).where(
+                        and_(
+                            MailFolder.account_id == account.id,
+                            MailFolder.imap_name == account.sent_folder_imap_name,
+                        )
+                    )
+                )
+            ).scalar_one_or_none()
+        else:
+            sent_folder = (
+                await db.execute(
+                    select(MailFolder).where(
+                        and_(
+                            MailFolder.account_id == account.id,
+                            MailFolder.imap_name.in_(
+                                ["Sent", "INBOX.Sent", "Sent Items", "Sent Mail"]
+                            ),
+                        )
+                    )
+                )
+            ).scalar_one_or_none()
+
+            if not sent_folder:
+                sent_folder = (
+                    await db.execute(
+                        select(MailFolder).where(
+                            and_(
+                                MailFolder.account_id == account.id,
+                                MailFolder.is_standard.is_(True),
+                                MailFolder.imap_name.ilike("%sent%"),
+                            )
+                        )
+                    )
+                ).scalar_one_or_none()
+
+        if sent_folder:
+            thread_id = _compute_thread_id(msg_id, references_header or "", in_reply_to)
+            sent_mail = Mail(
+                tenant_id=tenant_id,
+                account_id=account.id,
+                folder_id=sent_folder.id,
+                message_id=msg_id,
+                thread_id=thread_id,
+                in_reply_to=in_reply_to,
+                references_header=references_header,
+                subject=subject,
+                from_address=account.email_address,
+                to_addresses=", ".join(to_addrs),
+                cc_addresses=", ".join(cc_addrs),
+                bcc_addresses=", ".join(bcc_addrs),
+                body_text=body_text or _strip_html(body_html),
+                body_html=body_html,
+                body_html_sanitized=sanitize_html(body_html),
+                is_seen=True,
+                is_answered=bool(in_reply_to),
+                sent_at=datetime.now(UTC),
+            )
+            db.add(sent_mail)
+            await db.flush()
+
+            # Upload sent mail to IMAP Sent folder via APPEND
+            try:
+                imap_client = aioimaplib.IMAP4_SSL(host=account.imap_host, port=account.imap_port)
+                await imap_client.wait_hello_from_server()
+                await imap_client.login(account.username, password)
+                # Build raw email bytes for APPEND
+                raw_email_bytes = msg.as_bytes()
+                append_resp = await imap_client.append(
+                    sent_folder.imap_name,
+                    r'(\Seen)',
+                    None,
+                    raw_email_bytes,
+                )
+                if append_resp.result == 'OK':
+                    logger.info("send_mail: uploaded sent mail to IMAP folder %s", sent_folder.imap_name)
+                    # Retrieve the new UID for the appended mail by searching for its Message-ID
+                    try:
+                        await imap_client.select(sent_folder.imap_name)
+                        search_resp = await imap_client.uid_search(f'HEADER Message-ID "{msg_id}"')
+                        uid_raw = search_resp[1][0] if search_resp[1] and search_resp[1][0] else b''
+                        if isinstance(uid_raw, (bytes, bytearray)) and uid_raw:
+                            new_uids = uid_raw.decode().split()
+                            if new_uids:
+                                sent_mail.imap_uid = new_uids[0]
+                                logger.info("send_mail: set imap_uid=%s for sent mail %s", new_uids[0], sent_mail.id)
+                    except Exception as uid_exc:
+                        logger.warning("send_mail: could not retrieve UID after APPEND: %s", uid_exc)
+                else:
+                    logger.warning("send_mail: IMAP APPEND failed for sent folder %s: %s", sent_folder.imap_name, append_resp)
+                await imap_client.logout()
+            except Exception as imap_exc:
+                logger.warning("send_mail: IMAP APPEND failed (non-critical): %s", imap_exc)
+
+        # ── Notification: mail sent ──
+        try:
+            await create_notification(
+                db, tenant_id, user_id,
+                "mail_sent",
+                "E-Mail gesendet",
+                subject,
+            )
+            await db.flush()
+        except Exception:
+            logger.debug("Ignored exception in mail service", exc_info=True)
+
+        return {"status": "sent", "message_id": msg_id}
+    except Exception as e:
+        # ── Notification: send error ──
+        try:
+            await create_notification(
+                db, tenant_id, user_id,
+                "mail_send_error",
+                "E-Mail konnte nicht gesendet werden",
+                str(e),
+            )
+            await db.flush()
+        except Exception:
+            logger.debug("Ignored exception in mail service", exc_info=True)
+        return {"status": "error", "error": str(e)}
+
+
+async def reply_to_mail(
+    db: AsyncSession,
+    *,
+    tenant_id: uuid.UUID,
+    user_id: uuid.UUID,
+    original_mail: Mail,
+    account: MailAccount,
+    body_html: str,
+    body_text: str = "",
+    reply_to_all: bool = False,
+    signature: MailSignature | None = None,
+) -> dict:
+    """Reply to a mail, setting In-Reply-To and References headers (F-MAIL-02)."""
+    to_addrs = [original_mail.from_address]
+    if reply_to_all and original_mail.cc_addresses:
+        to_addrs.extend([a.strip() for a in original_mail.cc_addresses.split(",") if a.strip()])
+
+    refs = original_mail.references_header or ""
+    new_refs = f"{refs} {original_mail.message_id}".strip()
+
+    result = await send_mail_via_smtp(
+        db,
+        tenant_id=tenant_id,
+        user_id=user_id,
+        account=account,
+        to_addrs=to_addrs,
+        subject=f"Re: {original_mail.subject}".replace("Re: Re: ", "Re: "),
+        body_html=body_html,
+        body_text=body_text,
+        in_reply_to=original_mail.message_id,
+        references_header=new_refs,
+        signature=signature,
+    )
+
+    # Mark original as answered
+    original_mail.is_answered = True
+    await db.flush()
+    return result
+
+
+async def forward_mail(
+    db: AsyncSession,
+    *,
+    tenant_id: uuid.UUID,
+    user_id: uuid.UUID,
+    original_mail: Mail,
+    account: MailAccount,
+    to_addrs: list[str],
+    cc_addrs: list[str] = None,
+    body_html: str = "",
+    body_text: str = "",
+    signature: MailSignature | None = None,
+) -> dict:
+    """Forward a mail with original as forwarded content (F-MAIL-02)."""
+    fwd_subject = f"Fwd: {original_mail.subject}".replace("Fwd: Fwd: ", "Fwd: ")
+    fwd_body = (
+        f"<br><br>----- Original Message -----<br>"
+        f"From: {original_mail.from_address}<br>"
+        f"Subject: {original_mail.subject}<br><br>"
+        f"{original_mail.body_html or original_mail.body_text}"
+    )
+    full_html = body_html + fwd_body
+    full_text = (body_text or _strip_html(body_html)) + "\n\n----- Original Message -----\n"
+
+    result = await send_mail_via_smtp(
+        db,
+        tenant_id=tenant_id,
+        user_id=user_id,
+        account=account,
+        to_addrs=to_addrs,
+        cc_addrs=cc_addrs or [],
+        subject=fwd_subject,
+        body_html=full_html,
+        body_text=full_text,
+        signature=signature,
+    )
+
+    original_mail.is_forwarded = True
+    await db.flush()
+    return result
+
+