Send CfP emails via a queue

apps/admin/email.py

@@ -123,6 +123,7 @@ def email():
                 form.text.data,
                 reason=reason,
             )
+            db.session.commit()
             flash(f"Email queued for sending to {len(users)} users")
             return redirect(url_for(".email"))
 

apps/base/scheduled_tasks.py

@@ -1,33 +1,66 @@
 from flask import current_app as app
+from sqlalchemy import func, select
 
 from main import db, mail
-from models.email import EmailJobRecipient
+from models.email import Email, EmailJobRecipient
 from models.scheduled_task import scheduled_task
 from models.volunteer.notify import VolunteerNotifyRecipient
 
 from ..config import config
 
 
 @scheduled_task(minutes=1)
-def send_emails():
-    """Send queued emails, allowing for failure"""
+def send_transactional_emails():
+    """
+    Send queued non-bulk emails, allowing for failure.
+
+    As the job only runs once a minute, this isn't suitable for time-sensitive emails,
+    but they'll usually be sent in-line anyway.
+    """
+    count = 0
+
+    emails = list(db.session.scalars(select(Email).where(Email.sent_at.is_(None))))
+    for email in emails:
+        count += send_transactional_email(email)
+    return count
+
+
+def send_transactional_email(email: Email) -> int:
+    sent_count: int = mail.send_mail(
+        subject=email.subject,
+        from_email=email.from_email,
+        recipient_list=[email.recipient.email],
+        message=email.text_body,
+        html_message=email.html_body,
+        fail_silently=True,
+    )
+    if sent_count > 0:
+        email.sent_at = func.now()
+        db.session.commit()
+    return sent_count
+
+
+@scheduled_task(minutes=1)
+def send_bulk_emails():
+    """Send queued bulk emails, allowing for failure"""
     count = 0
 
+    # Sends via apps/common/backends/bulk.py
     with mail.get_connection(app.config.get("BULK_MAIL_BACKEND")) as conn:
         for rec in EmailJobRecipient.query.filter(EmailJobRecipient.sent == False):
-            count += send_email(conn, rec)
+            count += send_bulk_email(conn, rec)
     return count
 
 
-def send_email(conn, rec):
+def send_bulk_email(conn, rec):
     sent_count = mail.send_mail(
         subject=rec.job.subject,
         message=rec.job.text_body,
+        html_message=rec.job.html_body,
         from_email=config.from_email("CONTACT_EMAIL"),
         recipient_list=[rec.user.email],
         fail_silently=True,
         connection=conn,
-        html_message=rec.job.html_body,
     )
     if sent_count > 0:
         rec.sent = True

apps/cfp_review/base.py

@@ -32,6 +32,7 @@
 from wtforms import FormField
 
 from apps.common import get_next_url
+from apps.common.email import enqueue_email
 from main import db, external_url, get_or_404
 from models.content import (
     SCHEDULE_ITEM_INFOS,
@@ -391,15 +392,18 @@ def send_email_for_proposal(proposal: Proposal, reason: ProposalEmailReason) ->
 
     app.logger.info("Sending %s email for proposal %s", reason, proposal.id)
 
-    msg = EmailMessage(subject, from_email=from_email_, to=[proposal.user.email])
-    msg.body = render_template(
+    text_body = render_template(
         template,
         user=proposal.user,
         proposal=proposal,
         reserve_ticket_link=app.config["RESERVE_LIST_TICKET_LINK"],
     )
-
-    msg.send()
+    enqueue_email(
+        recipient=proposal.user,
+        from_email=from_email_,
+        subject=subject,
+        text_body=text_body,
+    )
 
 
 @cfp_review.route("/proposals/<int:proposal_id>/convert", methods=["GET", "POST"])

apps/common/email.py

@@ -6,7 +6,8 @@
 from markupsafe import Markup
 
 from main import db, mail
-from models.email import EmailJob, EmailJobRecipient
+from models.email import Email, EmailJob, EmailJobRecipient
+from models.user import User
 
 from ..config import config as app_config
 
@@ -135,15 +136,27 @@ def preview_trusted_email(preview_address, subject, body):
 
 
 def enqueue_trusted_emails(users, subject, body, **kwargs):
-    """Queue an email for sending by the background email worker."""
+    """Queue a bulk email for sending by the background email worker."""
     job = EmailJob(
-        subject,
-        format_trusted_plaintext_email(body, **kwargs),
-        format_trusted_html_email(body, subject, **kwargs),
+        subject=subject,
+        text_body=format_trusted_plaintext_email(body, **kwargs),
+        html_body=format_trusted_html_email(body, subject, **kwargs),
     )
     db.session.add(job)
 
     for user in users:
-        db.session.add(EmailJobRecipient(job, user))
+        db.session.add(EmailJobRecipient(job=job, user=user))
+
 
-    db.session.commit()
+def enqueue_email(
+    recipient: User, from_email: str, subject: str, text_body: str, html_body: Markup | None = None
+) -> None:
+    """Queue a transactional email for sending by the background email worker."""
+    email = Email(
+        recipient=recipient,
+        from_email=from_email,
+        subject=subject,
+        text_body=text_body,
+        html_body=html_body,
+    )
+    db.session.add(email)

apps/villages/admin.py

@@ -190,6 +190,7 @@ def admin_email_owners() -> ResponseReturnValue:
 
         if form.send.data is True:
             enqueue_trusted_emails(users, form.subject.data, form.text.data)
+            db.session.commit()
             flash(f"Email queued for sending to {users.count()} users")
             return redirect(url_for(".admin_email_owners"))
 

migrations/versions/c039b5838730_add_email.py

@@ -0,0 +1,43 @@
+"""Add email
+
+Revision ID: c039b5838730
+Revises: a1fe3b750f1e
+Create Date: 2026-05-03 20:24:01.858029
+
+"""
+
+# revision identifiers, used by Alembic.
+revision = 'c039b5838730'
+down_revision = 'a1fe3b750f1e'
+
+from alembic import op
+import sqlalchemy as sa
+
+
+def upgrade():
+    # ### commands auto generated by Alembic - please adjust! ###
+    op.create_table('email',
+    sa.Column('id', sa.Integer(), nullable=False),
+    sa.Column('recipient_id', sa.Integer(), nullable=False),
+    sa.Column('from_email', sa.String(), nullable=False),
+    sa.Column('subject', sa.String(), nullable=False),
+    sa.Column('text_body', sa.String(), nullable=False),
+    sa.Column('html_body', sa.String(), nullable=True),
+    sa.Column('created', sa.DateTime(), nullable=False),
+    sa.Column('sent_at', sa.DateTime(), nullable=True),
+    sa.ForeignKeyConstraint(['recipient_id'], ['user.id'], name=op.f('fk_email_recipient_id_user')),
+    sa.PrimaryKeyConstraint('id', name=op.f('pk_email'))
+    )
+    with op.batch_alter_table('email', schema=None) as batch_op:
+        batch_op.create_index(batch_op.f('ix_email_sent_at'), ['sent_at'], unique=False)
+
+    # ### end Alembic commands ###
+
+
+def downgrade():
+    # ### commands auto generated by Alembic - please adjust! ###
+    with op.batch_alter_table('email', schema=None) as batch_op:
+        batch_op.drop_index(batch_op.f('ix_email_sent_at'))
+
+    op.drop_table('email')
+    # ### end Alembic commands ###

models/email.py

@@ -7,7 +7,7 @@
 
 from . import BaseModel, naive_utcnow
 
-__all__ = ["EmailJob", "EmailJobRecipient"]
+__all__ = ["Email", "EmailJob", "EmailJobRecipient"]
 
 
 class EmailJob(BaseModel):
@@ -18,11 +18,6 @@ class EmailJob(BaseModel):
     html_body: Mapped[str]
     created: Mapped[datetime] = mapped_column(default=naive_utcnow)
 
-    def __init__(self, subject, text_body, html_body):
-        self.subject = subject
-        self.text_body = text_body
-        self.html_body = html_body
-
     @classmethod
     def get_export_data(cls):
         jobs = cls.query.with_entities(
@@ -38,19 +33,35 @@ class EmailJobRecipient(BaseModel):
     id: Mapped[int] = mapped_column(primary_key=True)
     user_id: Mapped[int] = mapped_column(ForeignKey("user.id"))
     job_id: Mapped[int] = mapped_column(ForeignKey("email_job.id"))
+    # TODO: replace with a timestamp like Email
     sent: Mapped[bool] = mapped_column(default=False)
 
     user: Mapped[User] = relationship()
     job: Mapped[EmailJob] = relationship()
 
-    def __init__(self, job, user):
-        self.job = job
-        self.user = user
-
 
 EmailJob.recipient_count = column_property(
     select(func.count(EmailJobRecipient.job_id))
     .where(EmailJobRecipient.job_id == EmailJob.id)
     .scalar_subquery(),
     deferred=True,
 )
+
+
+class Email(BaseModel):
+    """
+    Transactional (i.e. non-bulk) email, for things like CfP updates.
+    Having this in the DB allows us to link it to the rest of the database transaction.
+    """
+
+    __tablename__ = "email"
+    id: Mapped[int] = mapped_column(primary_key=True)
+    recipient_id: Mapped[int] = mapped_column(ForeignKey("user.id"))
+    from_email: Mapped[str]
+    subject: Mapped[str]
+    text_body: Mapped[str]
+    html_body: Mapped[str | None]
+    created: Mapped[datetime] = mapped_column(default=naive_utcnow)
+    sent_at: Mapped[datetime | None] = mapped_column(index=True)
+
+    recipient: Mapped[User] = relationship()