fix: embed uploaded logo in emails

backend/bot/services/email_auth_service.py

@@ -10,13 +10,13 @@ from dataclasses import dataclass
 from datetime import datetime, timedelta, timezone
 from email.message import EmailMessage
 from email.utils import formataddr
-from typing import Optional
+from typing import Optional, Sequence
 
 from sqlalchemy import select, update
 from sqlalchemy.ext.asyncio import AsyncSession
 
 from bot.middlewares.i18n import JsonI18n
-from bot.services.email_templates import EmailContent, render_login_code
+from bot.services.email_templates import EmailContent, EmailInlineImage, render_login_code
 from bot.services.message_audit import log_user_message_delivery
 from config.settings import Settings
 from db.dal import security_dal, user_dal
@@ -453,6 +453,7 @@ class EmailAuthService:
         subject: str,
         body: str,
         html_body: Optional[str] = None,
+        inline_images: Sequence[EmailInlineImage] = (),
     ) -> None:
         await asyncio.to_thread(
             self._send_custom_email_sync,
@@ -460,6 +461,7 @@ class EmailAuthService:
             subject=subject,
             body=body,
             html_body=html_body,
+            inline_images=inline_images,
         )
 
     async def send_rendered_email(
@@ -473,6 +475,7 @@ class EmailAuthService:
             subject=content.subject,
             body=content.text,
             html_body=content.html,
+            inline_images=content.inline_images,
         )
 
     def _send_code_email_sync(
@@ -493,17 +496,13 @@ class EmailAuthService:
             i18n=self.i18n,
         )
 
-        message = EmailMessage()
+        message = self._build_email_message(
-        message["Subject"] = content.subject
+            email=email,
-        message["From"] = formataddr(
+            subject=content.subject,
-            (
+            body=content.text,
-                self.settings.SMTP_FROM_NAME or self.settings.WEBAPP_TITLE,
+            html_body=content.html,
-                self.settings.SMTP_FROM_EMAIL or "",
+            inline_images=content.inline_images,
         )
-        )
-        message["To"] = email
-        message.set_content(content.text)
-        message.add_alternative(content.html, subtype="html")
 
         context = ssl.create_default_context()
         smtp_host = self.settings.SMTP_HOST
@@ -554,19 +553,15 @@ class EmailAuthService:
         subject: str,
         body: str,
         html_body: Optional[str] = None,
+        inline_images: Sequence[EmailInlineImage] = (),
     ) -> None:
-        message = EmailMessage()
+        message = self._build_email_message(
-        message["Subject"] = subject
+            email=email,
-        message["From"] = formataddr(
+            subject=subject,
-            (
+            body=body,
-                self.settings.SMTP_FROM_NAME or self.settings.WEBAPP_TITLE,
+            html_body=html_body,
-                self.settings.SMTP_FROM_EMAIL or "",
+            inline_images=inline_images,
         )
-        )
-        message["To"] = email
-        message.set_content(body)
-        if html_body:
-            message.add_alternative(html_body, subtype="html")
 
         context = ssl.create_default_context()
         smtp_host = self.settings.SMTP_HOST
@@ -610,6 +605,64 @@ class EmailAuthService:
         if last_error:
             raise last_error
 
+    def _build_email_message(
+        self,
+        *,
+        email: str,
+        subject: str,
+        body: str,
+        html_body: Optional[str] = None,
+        inline_images: Sequence[EmailInlineImage] = (),
+    ) -> EmailMessage:
+        message = EmailMessage()
+        message["Subject"] = subject
+        message["From"] = formataddr(
+            (
+                self.settings.SMTP_FROM_NAME or self.settings.WEBAPP_TITLE,
+                self.settings.SMTP_FROM_EMAIL or "",
+            )
+        )
+        message["To"] = email
+        message.set_content(body)
+        if html_body:
+            message.add_alternative(html_body, subtype="html")
+            self._attach_inline_images(message, inline_images)
+        return message
+
+    @staticmethod
+    def _attach_inline_images(
+        message: EmailMessage,
+        inline_images: Sequence[EmailInlineImage],
+    ) -> None:
+        if not inline_images:
+            return
+        html_part = message.get_body(("html",))
+        if html_part is None:
+            return
+
+        for image in inline_images:
+            content_type = (image.content_type or "").split(";", 1)[0].strip().lower()
+            if "/" not in content_type:
+                continue
+            maintype, subtype = content_type.split("/", 1)
+            if maintype != "image" or not subtype:
+                continue
+
+            body = bytes(image.data or b"")
+            content_id = (image.content_id or "").strip()
+            if not body or not content_id:
+                continue
+
+            cid_header = content_id
+            if not (cid_header.startswith("<") and cid_header.endswith(">")):
+                cid_header = f"<{cid_header}>"
+            html_part.add_related(
+                body,
+                maintype=maintype,
+                subtype=subtype,
+                cid=cid_header,
+            )
+
     def _send_message_via_smtp(
         self,
         *,

backend/bot/services/email_templates.py

@@ -12,6 +12,7 @@ from __future__ import annotations
 import html
 import re
 from dataclasses import dataclass
+from pathlib import Path
 from typing import TYPE_CHECKING, Optional, Sequence, Tuple
 from urllib.parse import urlsplit
 
@@ -27,6 +28,27 @@ _TEXT_MUTED = "#9aa3b2"
 _TEXT_DIM = "#5d6573"
 _DEFAULT_ACCENT = "#00fe7a"
 _HEX_RE = re.compile(r"^#(?:[0-9a-fA-F]{3}|[0-9a-fA-F]{6})$")
+_EMAIL_LOGO_CONTENT_ID = "webapp-logo"
+_WEBAPP_UPLOADED_LOGO_PATH = "/webapp-uploaded-logo"
+_WEBAPP_UPLOADED_LOGO_DIR = Path(__file__).resolve().parents[3] / "data" / "webapp-logo" / "uploads"
+_WEBAPP_LOGO_MAX_BYTES = 2 * 1024 * 1024
+_UPLOADED_LOGO_RE = re.compile(r"logo-[0-9a-f]{16}\.(?:gif|ico|jpe?g|png|svg|webp)")
+_LOGO_CONTENT_TYPES = {
+    ".gif": "image/gif",
+    ".ico": "image/x-icon",
+    ".jpg": "image/jpeg",
+    ".jpeg": "image/jpeg",
+    ".png": "image/png",
+    ".svg": "image/svg+xml",
+    ".webp": "image/webp",
+}
+
+
+@dataclass(frozen=True)
+class EmailInlineImage:
+    content_id: str
+    content_type: str
+    data: bytes
 
 
 @dataclass(frozen=True)
@@ -34,6 +56,13 @@ class EmailContent:
     subject: str
     text: str
     html: str
+    inline_images: Tuple[EmailInlineImage, ...] = ()
+
+
+@dataclass(frozen=True)
+class _EmailLayout:
+    html: str
+    inline_images: Tuple[EmailInlineImage, ...] = ()
 
 
 def _safe_color(value: Optional[str]) -> str:
@@ -57,6 +86,55 @@ def _public_logo_url(settings: Settings) -> Optional[str]:
     return raw
 
 
+def _uploaded_logo_filename(url: str) -> Optional[str]:
+    parsed = urlsplit(str(url or ""))
+    path = parsed.path if parsed.scheme or parsed.netloc else str(url or "")
+    prefix = f"{_WEBAPP_UPLOADED_LOGO_PATH}/"
+    if not path.startswith(prefix):
+        return None
+    filename = path.removeprefix(prefix)
+    return filename if _UPLOADED_LOGO_RE.fullmatch(filename) else None
+
+
+def _inline_uploaded_logo(settings: Settings) -> Optional[EmailInlineImage]:
+    filename = _uploaded_logo_filename((settings.WEBAPP_LOGO_URL or "").strip())
+    if not filename:
+        return None
+
+    content_type = _LOGO_CONTENT_TYPES.get(Path(filename).suffix.lower())
+    if not content_type:
+        return None
+
+    try:
+        uploads_dir = _WEBAPP_UPLOADED_LOGO_DIR.resolve()
+        logo_path = (uploads_dir / filename).resolve()
+        logo_path.relative_to(uploads_dir)
+        body = logo_path.read_bytes()
+    except (OSError, ValueError):
+        return None
+
+    if not body or len(body) > _WEBAPP_LOGO_MAX_BYTES:
+        return None
+
+    return EmailInlineImage(
+        content_id=_EMAIL_LOGO_CONTENT_ID,
+        content_type=content_type,
+        data=body,
+    )
+
+
+def _email_logo(settings: Settings) -> Tuple[Optional[str], Tuple[EmailInlineImage, ...]]:
+    inline_logo = _inline_uploaded_logo(settings)
+    if inline_logo:
+        return f"cid:{inline_logo.content_id}", (inline_logo,)
+
+    public_url = _public_logo_url(settings)
+    if public_url:
+        return public_url, ()
+
+    return None, ()
+
+
 def _brand_title(settings: Settings) -> str:
     title = (settings.WEBAPP_TITLE or "").strip()
     return title or "Subscription"
@@ -96,10 +174,10 @@ def _layout(
     intro_html: str,
     body_html: str,
     footer_html: str,
-) -> str:
+) -> _EmailLayout:
     accent = _safe_color(settings.WEBAPP_PRIMARY_COLOR)
     brand_title = html.escape(_brand_title(settings))
-    logo_url = _public_logo_url(settings)
+    logo_url, inline_images = _email_logo(settings)
     html_lang = html.escape((language_code or "en").replace("_", "-"), quote=True)
     logo_block = ""
     if logo_url:
@@ -109,7 +187,7 @@ def _layout(
             f'border-radius:16px;">'
         )
 
-    return f"""<!DOCTYPE html>
+    layout_html = f"""<!DOCTYPE html>
 <html lang="{html_lang}" xmlns="http://www.w3.org/1999/xhtml">
 <head>
 <meta charset="utf-8">
@@ -149,6 +227,16 @@ def _layout(
 </body>
 </html>
 """  # noqa: E501
+    return _EmailLayout(html=layout_html, inline_images=inline_images)
+
+
+def _email_content(*, subject: str, text: str, layout: _EmailLayout) -> EmailContent:
+    return EmailContent(
+        subject=subject,
+        text=text,
+        html=layout.html,
+        inline_images=layout.inline_images,
+    )
 
 
 def _info_rows_html(rows: Sequence[Tuple[str, str]]) -> str:
@@ -317,7 +405,7 @@ def render_login_code(
         body_html=body_html,
         footer_html=footer,
     )
-    return EmailContent(subject=subject, text="\n".join(text_lines), html=rendered)
+    return _email_content(subject=subject, text="\n".join(text_lines), layout=rendered)
 
 
 def render_account_merged(
@@ -370,7 +458,7 @@ def render_account_merged(
         body_html=body_html,
         footer_html=footer,
     )
-    return EmailContent(subject=subject, text=text, html=rendered)
+    return _email_content(subject=subject, text=text, layout=rendered)
 
 
 def render_payment_success(
@@ -504,7 +592,7 @@ def render_payment_success(
         body_html="".join(body_parts),
         footer_html=footer,
     )
-    return EmailContent(subject=subject, text="\n".join(text_lines), html=rendered)
+    return _email_content(subject=subject, text="\n".join(text_lines), layout=rendered)
 
 
 def render_user_notification(
@@ -565,7 +653,7 @@ def render_user_notification(
                 ),
             ]
         )
-    return EmailContent(subject=final_subject, text="\n".join(text_lines), html=rendered)
+    return _email_content(subject=final_subject, text="\n".join(text_lines), layout=rendered)
 
 
 def render_subscription_expiring(
@@ -629,7 +717,7 @@ def render_subscription_expiring(
         body_html="".join(body_parts),
         footer_html=footer,
     )
-    return EmailContent(subject=subject, text="\n".join(text_lines), html=rendered)
+    return _email_content(subject=subject, text="\n".join(text_lines), layout=rendered)
 
 
 def _subscription_lifecycle_title(
@@ -731,7 +819,7 @@ def render_subscription_lifecycle_notification(
                 ),
             ]
         )
-    return EmailContent(subject=subject, text="\n".join(text_lines), html=rendered)
+    return _email_content(subject=subject, text="\n".join(text_lines), layout=rendered)
 
 
 def _support_email(
@@ -783,7 +871,7 @@ def _support_email(
     ]
     if safe_url:
         text_lines.extend(["", safe_url])
-    return EmailContent(subject=subject, text="\n".join(text_lines), html=rendered)
+    return _email_content(subject=subject, text="\n".join(text_lines), layout=rendered)
 
 
 def render_support_new_ticket_admin(

tests/test_email_auth_service.py

@@ -0,0 +1,41 @@
+from types import SimpleNamespace
+
+from bot.services.email_auth_service import EmailAuthService
+from bot.services.email_templates import EmailInlineImage
+
+
+def _settings():
+    return SimpleNamespace(
+        SMTP_FROM_NAME="Mini Shop",
+        SMTP_FROM_EMAIL="noreply@example.com",
+        WEBAPP_TITLE="Mini Shop",
+    )
+
+
+def test_build_email_message_attaches_inline_images_to_html_part():
+    service = EmailAuthService(_settings())
+
+    message = service._build_email_message(
+        email="user@example.com",
+        subject="Login code",
+        body="Your code: 123456",
+        html_body='<img src="cid:webapp-logo" alt="">',
+        inline_images=(
+            EmailInlineImage(
+                content_id="webapp-logo",
+                content_type="image/png",
+                data=b"\x89PNG\r\n\x1a\nlogo",
+            ),
+        ),
+    )
+
+    related_part = message.get_body(("related",))
+    assert related_part is not None
+    html_part = related_part.get_body(("html",))
+    assert html_part is not None
+    related_images = [part for part in related_part.iter_attachments()]
+
+    assert len(related_images) == 1
+    assert related_images[0].get_content_type() == "image/png"
+    assert related_images[0]["Content-ID"] == "<webapp-logo>"
+    assert related_images[0].get_content_disposition() == "inline"

tests/test_email_localization.py

@@ -6,6 +6,7 @@ from pathlib import Path
 from types import SimpleNamespace
 
 from bot.middlewares.i18n import JsonI18n
+from bot.services import email_templates as email_templates_module
 from bot.services.email_templates import (
     EmailContent,
     render_account_merged,
@@ -255,6 +256,49 @@ def test_all_email_template_variants_render_without_raw_locale_keys():
             _assert_content_is_localized(content, language)
 
 
+def test_uploaded_webapp_logo_is_embedded_inline(tmp_path, monkeypatch):
+    uploads_dir = tmp_path / "uploads"
+    uploads_dir.mkdir()
+    filename = "logo-1111111111111111.png"
+    logo_body = b"\x89PNG\r\n\x1a\nlogo"
+    (uploads_dir / filename).write_bytes(logo_body)
+    monkeypatch.setattr(email_templates_module, "_WEBAPP_UPLOADED_LOGO_DIR", uploads_dir)
+
+    settings = _settings()
+    settings.WEBAPP_LOGO_URL = f"/webapp-uploaded-logo/{filename}"
+
+    content = render_login_code(
+        settings,
+        code="123456",
+        language_code="en",
+        purpose="login",
+        i18n=_i18n("en"),
+    )
+
+    assert 'src="cid:webapp-logo"' in content.html
+    assert len(content.inline_images) == 1
+    inline_logo = content.inline_images[0]
+    assert inline_logo.content_id == "webapp-logo"
+    assert inline_logo.content_type == "image/png"
+    assert inline_logo.data == logo_body
+
+
+def test_public_https_webapp_logo_remains_external():
+    settings = _settings()
+    settings.WEBAPP_LOGO_URL = "https://cdn.example.com/logo.png"
+
+    content = render_login_code(
+        settings,
+        code="123456",
+        language_code="en",
+        purpose="login",
+        i18n=_i18n("en"),
+    )
+
+    assert 'src="https://cdn.example.com/logo.png"' in content.html
+    assert content.inline_images == ()
+
+
 def test_support_email_templates_use_russian_copy_for_russian_recipients():
     subjects = [content.subject for content in _all_rendered_email_variants("ru")[-4:]]