1776438 - Thunderbird silently failed to send message with 8-bit character in From address (fastmail, SMTPUTF8)

Status: RESOLVED INVALID

(Thunderbird :: Message Compose Window, defect)

Description

[Eric Moore]

I'm using 102.0b8 under Windows 11Pro. I added a multiple identity to my Fastmail IMAP account that used plus addressing, with a 8bit character in the optional string. It was emoore+Ã[e-mail]

When I tried to send a message using that From: address to my Gmail account I expected it to either send the message, or to get a error complaining about Fastmail not supported SMTPUTF8. Instead it did nothing other than close the window. No error, no message was sent, no saved copy in my Sent folder. I tried this three times in a row with the same results and then sent a message from my accounts main identity to the same recipient. That worked.

The lack of a copy of the saved message is not a bug because I don't enable Thunderbird saving a copy of the sent message. I use webmail settings to configure the SMTP server to do that when using a email client for specific From: addresses. The multiple identity is not one of them.

Thunderbird should never silently fail to send a message.

Comment 1

[Thomas D. (:thomas8)]

(In reply to Eric Moore from comment #0)

Hey Eric, thanks for your report. Can you please add proper STR, Actual Result, Expected Result in separate sections, with bullet points?
Did you add another identity in your TB IMAP account?

Comment 2

[Eric Moore]

"Did you add another identity in your TB IMAP account?"

Yes. "I added a multiple identity to my Fastmail IMAP account"

The accounts normal email address is [e-mail] . There is also a alias of [e-mail] (set via webmail GUI) . Its not configured as a multiple identity in Thunderbird.

I have no idea what "proper STR" means. No, I'm not going to rewrite the report. I've read https://bugzilla.mozilla.org/page.cgi?id=bug-writing.html before and I think you are taking parts of the "guidelines" way too literally.

Comment 3

[Alfred Peters [:infofrommozilla]]

(In reply to Eric Moore from comment #0)

I'm using 102.0b8 under Windows 11Pro. I added a multiple identity to my Fastmail IMAP account that used plus addressing, with a 8bit character in the optional string. It was emoore+Ã[e-mail]

Please check your version again.
This was fixed in Bug 1773672 and it works for me with TB102.0b8.

If it's still broken on your end, what makes your case different from Bug 1773672?

(In reply to Eric Moore from comment #2)

I have no idea what "proper STR" means.

STR = Steps To Reproduce

No, I'm not going to rewrite the report. I've read https://bugzilla.mozilla.org/page.cgi?id=bug-writing.html

| 1. Figure out the steps to reproduce a bug:

If we can't reproduce, we can't fix it.

Comment 4

[Eric Moore]

1. A multiple identity using ümläü[e-mail] works fine when I send a message from my Fastmail IMAP account to my Gmail IMAP account. I get the message in my Gmail account and there is a copy in my Fastmail Sent Items folder.

2. A multiple identity using emoore+Ã[e-mail] continues to fail. I briefly see the Sending message popup with the progress bar (so quick I didn't notice it before) but afterwards there is no sign of the message in my Gmail account or any error.

3. I edited that multiple identity to use a emooreÃ[e-mail] address, no longer using plus addressing. That causes the following error when sending a message to my gmail account:

Sending of the message failed.
An error occurred while sending mail. The mail server responded: Not authorized to send from this header address. Please check the message and try again.

4. I changed the ümläü[e-mail] multiple identity to use ümläü[e-mail] and tried to send to the gmail account. I also got:

Sending of the message failed.
An error occurred while sending mail. The mail server responded: Not authorized to send from this header address. Please check the message and try again.

I assume Fastmail allows anybody to send using the example.com domain but checks for a authorized username for other domains.

5. I created a erm4gh+ümläü[e-mail] multiple identity for my Gmail IMAP account. Its normal email address is [e-mail]. Using that multiple identity I tried to send a message to my [e-mail] address (my main identity for my Fastmail IMAP account).

I briefly see the Sending message popup with the progress bar but afterwards there is no sign of the message or any error.

6. Looking in the junk mail folder of my Fastmail account I see four "Undelivered mail return to sender" messages from the Mail Delivery System. Two were from this morning, two were from this afternoon. Except for date/time and ids they're identical. I don't know why they're in the junk mail folder rather than the inbox. Junk processing/adaptive junk mail controls are disabled for Thunderbird.

The Fastmail support team.
out.woutbound1

<[e-mail]>: host gmail-smtp-in.l.google.com[142.250.102.26] said: 555
5.5.2 Syntax error. hq2-20020a1709073f0200b00711dc331bfasi3969998ejc.765 -
gsmtp (in reply to MAIL FROM command)

Reporting-MTA: dns; mailout.west.internal
X-Postfix-Queue-ID: 152D732001C6
X-Postfix-Sender: rfc822; "emoore+\肻儀"@fastmail.com
Arrival-Date: Fri, 24 Jun 2022 13:26:16 -0400 (EDT)

Final-Recipient: rfc822; [e-mail]
Original-Recipient: rfc822;[e-mail]
Action: failed
Status: 5.5.2
Remote-MTA: dns; gmail-smtp-in.l.google.com
Diagnostic-Code: smtp; 555 5.5.2 Syntax error.
hq2-20020a1709073f0200b00711dc331bfasi3969998ejc.765 - gsmtp

The recipient is listed as emoore@+??xfastmail.com in Thunderbird's folder listing. I don't see a similar type of message in the Gmail spam folder (which also failed).

7. You wanted me to verify what version I'm using. I copied and pasted the following from help -> more troubleshooting information:

Application Basics

Name: Thunderbird
Version: 102.0b8
Build ID: 20220621172622
Distribution ID:

Update Channel: beta
User Agent: Mozilla/5.0 (Windows NT 10.0; Win64; x64; rv:102.0) Gecko/20100101 Thunderbird/102.0
OS: Windows_NT 10.0 22000
OS Theme:

Comment 5

[Ping Chen [:rnons] (away)]

Thanks for your detailed testing.

(In reply to Eric Moore from comment #4)

2. A multiple identity using emoore+Ã[e-mail] continues to fail. I briefly see the Sending message popup with the progress bar (so quick I didn't notice it before) but afterwards there is no sign of the message in my Gmail account or any error.

3. I edited that multiple identity to use a emooreÃ[e-mail] address, no longer using plus addressing. That causes the following error when sending a message to my gmail account:

Sending of the message failed.
An error occurred while sending mail. The mail server responded: Not authorized to send from this header address. Please check the message and try again.

For case 2, I got the same result as case 3. An error dialog was shown correctly.

5. I created a erm4gh+ümläü[e-mail] multiple identity for my Gmail IMAP account. Its normal email address is [e-mail]. Using that multiple identity I tried to send a message to my [e-mail] address (my main identity for my Fastmail IMAP account).

I briefly see the Sending message popup with the progress bar but afterwards there is no sign of the message or any error.

This worked for me, I sent a message to myself and received it correctly.

mailnews.smtp: C: MAIL FROM:<xxx+ümläü[e-mail]> BODY=8BITMIME SMTPUTF8 SIZE=444 SmtpClient.jsm:589:19
mailnews.smtp: S: 250 2.1.0 OK s1-20020a17090a880100b001ec8c53544esm2332961pjn.46 - gsmtp
mailnews.smtp: MAIL FROM successful, proceeding with 1 recipients SmtpClient.jsm:1146:17
mailnews.smtp: Adding recipient...

Can you go to the Config Editor, set mailnews.smtp.loglevel to All, to get some debug logs?

Comment 6

[Eric Moore]

I set mailnews.smtp.loglevel to All and retested using 102.0b8 . My fastmail IMAP account is a "basic" plan account with POP/IMAP/SMTP grandfathered in, due to a prior legacy account. I'm still using mail.messagingengine.com for both the IMAP and SMTP server. I'm reluctant to move to the newer servers (imap.fastmail.com and smtp.fastmail.com) as they require a application specific password.

Looking at my Gmail account I was surprised to see that I now only have the Fastmail SMTP server listed. However, help -> more troubleshooting information shows I'm using smtp.gmail.com. I added a comment to Bug 1773123 . I deleted the junk mail folder in Fastmail and the spam folder in Gmail and Outlooks. I cleared the error console.

1. Send using ümläü[e-mail] multiple identity from Fastmail to Gmail

That worked before. This time I got:

Sending of the message failed.
An error occurred while sending mail. The mail server responded: Not authorised to send from this header address. Please check the message and try again.

I then tried again where I used "Customize From: Address" rather than using the multiple identity. Same result.

2. Send using emoore+Ã[e-mail] multiple identity from Fastmail to Gmail

No error message popup. In the junk mail folder I got a Undelivered Mail Returned To Sender sent to emoore@??[e-mail]

The Fastmail support team.
out.woutbound1

<[e-mail]>: host gmail-smtp-in.l.google.com[142.250.102.27] said: 555
5.5.2 Syntax error. x1-20020aa7dac1000000b0043564aec56bsi11601170eds.52 -
gsmtp (in reply to MAIL FROM command)

Reporting-MTA: dns; mailout.west.internal
X-Postfix-Queue-ID: 423343200583
X-Postfix-Sender: rfc822; "emoore+\肻儀"@fastmail.com
Arrival-Date: Mon, 27 Jun 2022 08:02:41 -0400 (EDT)

Final-Recipient: rfc822; [e-mail]
Original-Recipient: rfc822;[e-mail]
Action: failed
Status: 5.5.2
Remote-MTA: dns; gmail-smtp-in.l.google.com
Diagnostic-Code: smtp; 555 5.5.2 Syntax error.
x1-20020aa7dac1000000b0043564aec56bsi11601170eds.52 - gsmtp

I tried it again. Same result.

3. Send using emooreÃ[e-mail] multiple identity from Fastmail to Gmail

I got:

Sending of the message failed.
An error occurred while sending mail. The mail server responded: Not authorised to send from this header address. Please check the message and try again.

4. Send using erm4gh+ümläü[e-mail] multiple identity from Gmail to Fastmail

This succeeded. I got the message in the fastmail inbox, the gmail inbox and the gmail sent items. I did not expect it in the gmail inbox since I sent it from gmail.

"show only display name for people in my address book" is UNchecked. I saw the display name (Eric Moore w/umlauts) in the from column for the new message in my fastmail inbox folder listing. I expected to see the email address. Looking at the headers in the message pane it shows the display name plus my normal email address ([e-mail]), not erm4gh+ümläü[e-mail] .

5. Send using erm4gh+ümläü[e-mail] multiple identity from Gmail to Outlook

This succeeded. identical to #4 except it doesn't hide the plus addresses (which are displayed correctly)

6. Send from [e-mail] to erm4gh+ümläü[e-mail]

Succeeded. I got a saved copy in outlook.com and a new copy in both the gmail inbox and sent items. I did not expect a new message in the sent items folder in Gmail. Looking at the raw message source I can see it was sent from outlook.com using the MS exchange server. Outlooks settings say it uses the smtp.office365.com smtp server. The only message filter I have in my Gmail IMAP account sets the message status to Junk if the subject includes SPAM . Its not set to junk.

The IMAP server directory for the Gmail IMAP account is set to [Gmail] to flatten the folder listing. Can this add another label to new mail?

The correspondent column in Gmail inbox is erm4gh+ümläü[e-mail] The message pane shows it was sent to erm4gh+ümläü[e-mail] .

Comment 7

[Eric Moore]

Attachment: smtp_retest.txt - smtp logging from error console when retested

Comment 8

[Alfred Peters [:infofrommozilla]]

Attached file smtp_retest.txt - smtp logging from error console when retested

I don't see any error there.

(In reply to Eric Moore from comment #6)

1. Send using ümläü[e-mail] multiple identity from Fastmail to Gmail

That worked before. This time I got:

An error occurred while sending mail. The mail server responded: Not authorised to send from this header address. Please check the message and try again.

3. Send using emooreÃ[e-mail] multiple identity from Fastmail to Gmail

Sending of the message failed.
An error occurred while sending mail. The mail server responded: Not authorised to send from this header address. Please check the message and try again.

1. & 3.:
   The fastmail server thinks you are not authorized to send from this account with this from address. If you disagree, you need to clarify this with Fastmail. There is nothing TB can do in this case.

2. Send using emoore+Ã[e-mail] multiple identity from Fastmail to Gmail

No error message popup. In the junk mail folder I got a Undelivered Mail Returned To Sender sent to emoore@??[e-mail]

So Fastmail accepted this address and the email was received.

<[e-mail]>: host gmail-smtp-in.l.google.com[142.250.102.27] said: 555
5.5.2 Syntax error. x1-20020aa7dac1000000b0043564aec56bsi11601170eds.52 -
gsmtp (in reply to MAIL FROM command)

But then there was a transmission error between Fastmail and Gmail. This is again something TB has no influence on.

Reporting-MTA: dns; mailout.west.internal
X-Postfix-Queue-ID: 423343200583
X-Postfix-Sender: rfc822; "emoore+\肻儀"@fastmail.com

The address seems to have been messed up. However, this may have happened only in the error report.

Comment 9

[Magnus Melin [:mkmelin]]

Seems we can close this?

Comment 10

[Eric Moore]

If I send a message using 102.1.0 between two gmail accounts using plus addressing that contains 8bit characters my copy of the sent message shows the correct From: address but the plus addressing is stripped in the received message (in both Thunderbird and webmail). X-Google-Original-From: Eric Moore <piscataqua+ümläü[e-mail]> is garbled (should have been piscataqua+ümläü[e-mail]) but that doesn't matter .

I looked into creating a alias in gmail webmail that contained 8bit characters but its not a real alias, I have to prove that I own that email address. I'm not willing to give them my smartphone number in order to create a new account that uses 8bit characters in the username .

So I'm closing this as it works as expected when using plus addressing between accounts that support smtputf8 and I don't have any accounts to properly test 8bit characters in usernames.