Email on push - multiple recipients break S/MIME signature

Summary

We use S/MIME to sign all of our outgoing email messages from our GitLab instance. This includes mails from the Email on Push feature. We unchecked "Send from committer". If there are multiple recipients in the list, only the first one will get the message signed correctly.

Steps to reproduce

1. Setup GitLab with SMIME for outgoing mails
2. Enable Emails on Push for a repository

• uncheck "Send from committer"
• enter multiple recipients, seperated by space or newline

3. Push to the repository

Example Project

This happens on our self-hosted GitLab instance.

What is the current bug behavior?

Only the first recipient will receive the mail correctly signed. All other recipients get SMIME errors.

What is the expected correct behavior?

All recipients receive a correctly signed message.

Output of checks

Results of GitLab environment info

Expand for output related to GitLab environment info

```
git ~ # gitlab-rake gitlab:env:info

System information
System:
Current User:	git
Using RVM:	no
Ruby Version:	2.6.5p114
Gem Version:	2.7.10
Bundler Version:1.17.3
Rake Version:	12.3.3
Redis Version:	5.0.7
Git Version:	2.24.1
Sidekiq Version:5.2.7
Go Version:	unknown

GitLab information
Version:	12.8.9
Revision:	f4e077c4310
Directory:	/opt/gitlab/embedded/service/gitlab-rails
DB Adapter:	PostgreSQL
DB Version:	10.12
URL:		https://git.***.de
HTTP Clone URL:	https://git.***.de/some-group/some-project.git
SSH Clone URL:	git@git.***.de:some-group/some-project.git
Using LDAP:	yes
Using Omniauth:	yes
Omniauth Providers: github

GitLab Shell
Version:	11.0.0
Repository storage paths:
- default: 	/data/git/repositories
GitLab Shell path:		/opt/gitlab/embedded/service/gitlab-shell
Git:		/opt/gitlab/embedded/bin/git
```

Results of GitLab application Check

Expand for output related to the GitLab application check

Checking GitLab subtasks ...

Checking GitLab Shell ...

GitLab Shell: ... GitLab Shell version >= 11.0.0 ? ... OK (11.0.0)
Running /opt/gitlab/embedded/service/gitlab-shell/bin/check
Internal API available: OK
Redis available via internal API: OK
gitlab-shell self-check successful

Checking GitLab Shell ... Finished

Checking Gitaly ...

Gitaly: ... default ... OK

Checking Gitaly ... Finished

Checking Sidekiq ...

Sidekiq: ... Running? ... yes
Number of Sidekiq processes ... 1

Checking Sidekiq ... Finished

Checking Incoming Email ...

Incoming Email: ... Checking Reply by email ...

IMAP server credentials are correct? ... yes
Init.d configured correctly? ... skipped
MailRoom running? ... skipped

Checking Reply by email ... Finished


Checking Incoming Email ... Finished

Checking LDAP ...

LDAP: ... Server: ldapmain
LDAP authentication... Anonymous. No `bind_dn` or `password` configured
LDAP users with access to your GitLab server (only showing the first 100 results)
	User output sanitized. Found 100 users of 100 limit.

Checking LDAP ... Finished

Checking GitLab App ...

Git configured correctly? ... yes
Database config exists? ... yes
All migrations up? ... yes
Database contains orphaned GroupMembers? ... no
GitLab config exists? ... yes
GitLab config up to date? ... yes
Log directory writable? ... yes
Tmp directory writable? ... yes
Uploads directory exists? ... yes
Uploads directory has correct permissions? ... yes
Uploads directory tmp has correct permissions? ... yes
Init script exists? ... skipped (omnibus-gitlab has no init script)
Init script up-to-date? ... skipped (omnibus-gitlab has no init script)
Projects have namespace: ... 
141/7 ... yes
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532/1394 ... yes
586/1395 ... yes
188/1397 ... yes
638/1398 ... yes
578/1399 ... yes
180/1401 ... yes
639/1402 ... yes
287/1403 ... yes
283/1404 ... yes
187/1405 ... yes
643/1406 ... yes
643/1407 ... yes
457/1408 ... yes
356/1410 ... yes
590/1411 ... yes
68/1413 ... yes
192/1414 ... yes
61/1415 ... yes
644/1416 ... yes
219/1417 ... yes
93/1418 ... yes
648/1419 ... yes
503/1420 ... yes
20/1421 ... yes
521/1423 ... yes
184/1424 ... yes
423/1425 ... yes
345/1426 ... yes
187/1427 ... yes
242/1428 ... yes
265/1429 ... yes
255/1431 ... yes
186/1432 ... yes
655/1433 ... yes
655/1434 ... yes
652/1435 ... yes
650/1436 ... yes
657/1437 ... yes
462/1440 ... yes
583/1441 ... yes
569/1442 ... yes
325/1443 ... yes
505/1444 ... yes
3/1445 ... yes
11/1446 ... yes
669/1448 ... yes
183/1450 ... yes
144/1451 ... yes
559/1452 ... yes
644/1454 ... yes
645/1456 ... yes
645/1457 ... yes
505/1458 ... yes
505/1459 ... yes
126/1460 ... yes
592/1461 ... yes
667/1463 ... yes
667/1464 ... yes
667/1465 ... yes
634/1466 ... yes
543/1467 ... yes
294/1468 ... yes
688/1469 ... yes
650/1470 ... yes
650/1471 ... yes
144/1472 ... yes
651/1473 ... yes
593/1474 ... yes
644/1476 ... yes
685/1477 ... yes
503/1479 ... yes
19/1480 ... yes
19/1481 ... yes
687/1482 ... yes
687/1483 ... yes
650/1485 ... yes
688/1487 ... yes
572/1488 ... yes
193/1489 ... yes
687/1490 ... yes
144/1491 ... yes
47/1492 ... yes
199/1493 ... yes
222/1495 ... yes
182/1496 ... yes
517/1497 ... yes
202/1498 ... yes
517/1499 ... yes
689/1500 ... yes
691/1501 ... yes
691/1502 ... yes
20/1503 ... yes
676/1504 ... yes
222/1506 ... yes
685/1507 ... yes
169/1508 ... yes
667/1509 ... yes
144/1510 ... yes
602/1511 ... yes
650/1512 ... yes
203/1513 ... yes
407/1514 ... yes
76/1515 ... yes
658/1517 ... yes
616/1518 ... yes
652/1519 ... yes
407/1521 ... yes
652/1522 ... yes
616/1523 ... yes
658/1524 ... yes
407/1525 ... yes
569/1527 ... yes
11/1528 ... yes
695/1529 ... yes
695/1531 ... yes
273/1532 ... yes
625/1533 ... yes
664/1534 ... yes
522/1535 ... yes
664/1536 ... yes
645/1537 ... yes
645/1538 ... yes
503/1539 ... yes
664/1541 ... yes
664/1542 ... yes
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51/1545 ... yes
255/1549 ... yes
637/1550 ... yes
222/1551 ... yes
5/1552 ... yes
192/1553 ... yes
200/1554 ... yes
621/1555 ... yes
699/1556 ... yes
240/1557 ... yes
701/1558 ... yes
664/1559 ... yes
402/1560 ... yes
702/1561 ... yes
813/1562 ... yes
554/1563 ... yes
180/1564 ... yes
141/1566 ... yes
652/1567 ... yes
651/1568 ... yes
465/1569 ... yes
11/1570 ... yes
354/1571 ... yes
548/1572 ... yes
5/1573 ... yes
549/1574 ... yes
547/1575 ... yes
544/1576 ... yes
708/1577 ... yes
559/1578 ... yes
193/1579 ... yes
222/1580 ... yes
664/1581 ... yes
709/1582 ... yes
703/1583 ... yes
203/1584 ... yes
505/1585 ... yes
621/1586 ... yes
203/1587 ... yes
554/1588 ... yes
664/1589 ... yes
141/1590 ... yes
566/1591 ... yes
602/1593 ... yes
27/1597 ... yes
451/1599 ... yes
451/1600 ... yes
719/1604 ... yes
503/1605 ... yes
644/1606 ... yes
451/1608 ... yes
255/1609 ... yes
203/1610 ... yes
485/1611 ... yes
31/1612 ... yes
631/1613 ... yes
192/1614 ... yes
630/1615 ... yes
727/1616 ... yes
670/1617 ... yes
691/1618 ... yes
691/1619 ... yes
427/1620 ... yes
505/1621 ... yes
729/1622 ... yes
55/1623 ... yes
730/1626 ... yes
721/1628 ... yes
721/1629 ... yes
294/1631 ... yes
479/1632 ... yes
602/1633 ... yes
602/1634 ... yes
202/1635 ... yes
203/1636 ... yes
721/1637 ... yes
410/1638 ... yes
313/1640 ... yes
503/1641 ... yes
569/1642 ... yes
744/1645 ... yes
744/1646 ... yes
534/1647 ... yes
325/1648 ... yes
27/1649 ... yes
295/1650 ... yes
193/1651 ... yes
344/1652 ... yes
325/1653 ... yes
706/1654 ... yes
134/1655 ... yes
755/1656 ... yes
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232/1658 ... yes
22/1659 ... yes
226/1660 ... yes
144/1661 ... yes
451/1663 ... yes
144/1664 ... yes
188/1665 ... yes
567/1667 ... yes
47/1668 ... yes
721/1669 ... yes
451/1670 ... yes
691/1671 ... yes
602/1672 ... yes
477/1673 ... yes
371/1674 ... yes
703/1675 ... yes
371/1676 ... yes
133/1677 ... yes
371/1678 ... yes
755/1679 ... yes
144/1680 ... yes
755/1681 ... yes
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94/1683 ... yes
691/1684 ... yes
691/1685 ... yes
756/1686 ... yes
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760/1688 ... yes
505/1690 ... yes
691/1691 ... yes
371/1692 ... yes
656/1693 ... yes
371/1696 ... yes
763/1698 ... yes
465/1699 ... yes
569/1700 ... yes
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592/1702 ... yes
394/1703 ... yes
237/1704 ... yes
642/1706 ... yes
187/1707 ... yes
427/1708 ... yes
31/1709 ... yes
10/1710 ... yes
775/1711 ... yes
775/1712 ... yes
775/1713 ... yes
691/1714 ... yes
621/1715 ... yes
777/1716 ... yes
667/1717 ... yes
777/1718 ... yes
394/1719 ... yes
534/1720 ... yes
607/1723 ... yes
3/1724 ... yes
710/1725 ... yes
139/1726 ... yes
2/1727 ... yes
782/1728 ... yes
255/1729 ... yes
775/1731 ... yes
181/1732 ... yes
786/1733 ... yes
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782/1735 ... yes
706/1736 ... yes
222/1737 ... yes
763/1738 ... yes
644/1739 ... yes
706/1740 ... yes
706/1741 ... yes
763/1742 ... yes
579/1743 ... yes
485/1744 ... yes
590/1745 ... yes
180/1746 ... yes
792/1747 ... yes
792/1748 ... yes
421/1749 ... yes
651/1750 ... yes
775/1751 ... yes
642/1753 ... yes
797/1754 ... yes
222/1755 ... yes
803/1757 ... yes
667/1758 ... yes
356/1760 ... yes
187/1761 ... yes
159/1762 ... yes
141/1763 ... yes
225/1764 ... yes
182/1765 ... yes
558/1766 ... yes
644/1767 ... yes
558/1768 ... yes
354/1769 ... yes
10/1770 ... yes
806/1771 ... yes
425/1772 ... yes
772/1773 ... yes
10/1775 ... yes
613/1776 ... yes
771/1777 ... yes
371/1778 ... yes
625/1779 ... yes
811/1781 ... yes
810/1782 ... yes
807/1783 ... yes
808/1784 ... yes
809/1785 ... yes
644/1787 ... yes
814/1788 ... yes
613/1791 ... yes
613/1792 ... yes
815/1796 ... yes
815/1797 ... yes
815/1798 ... yes
815/1799 ... yes
815/1800 ... yes
763/1801 ... yes
815/1802 ... yes
815/1803 ... yes
144/1806 ... yes
Redis version >= 2.8.0? ... yes
Ruby version >= 2.5.3 ? ... yes (2.6.5)
Git version >= 2.22.0 ? ... yes (2.24.1)
Git user has default SSH configuration? ... yes
Active users: ... 349
Is authorized keys file accessible? ... yes

Checking GitLab App ... Finished


Checking GitLab subtasks ... Finished

Possible fixes

I have no idea on this one.

/cc @dlouzan More strange SMIME behaviour - have you noticed this too?