What a bad introduction to fastmail

[botolo]

Dear All,

Being a happy user of fastmail, I convinced my girlfriend to open an account and to forward his work's email to fastmail and use the "personalities" function to send email as sent from the work account.

Well, while at the beginning everything seemed to work fine, starting from yesterday, without any warning, fastmail stopped delivering her messages sent to @berkeley.edu account. She sent several emails but it seems that nobody received them.

And what is worst: yesterday morning she sent a job application to a professor who was looking for a research assistant on a first come-first served basis. Not having heard from him, she sent again the same application in the evening with her old hotmail account. Guess what, the professor replied immediately saying that he did not receive the first email, that he was very sorry because he liked her resume but the position had been already filled.

And now she hates fastmail, and I can understand her.

How could this happen?!? Without any warning, any error message, any delivery issue report, nothing!!

[botolo]

the same does not happen with gmail. every email sent from gmail using her work address is correctly delivered. and it is what services like pobox ground their services.

[David]

Originally Posted by botolo

the same does not happen with gmail. every email sent from gmail using her work address is correctly delivered. and it is what services like pobox ground their services.

I deleted my earlier post botolo because it was not (strictly) correct. Creating a personality (of an account you own) though legal in the sense that it is not a forgery is in fact a dangerous one; you are sending mail from an SMTP server that is not the one of the account 'from address' - this is a dangerous tactic (especially for business email) imo.

[botolo]

the problem is that her work account offers small storage quota and this is why I suggested her to buy a fastmail account for storage and have all emails forwarded to the fm account and send emails from fm smtp with personalities set up.

and in any case, i don't understand why gmail is not having these problems.

[David]

Originally Posted by botolo

the problem is that her work account offers small storage quota and this is why I suggested her to buy a fastmail account for storage and have all emails forwarded to the fm account and send emails from fm smtp with personalities set up.

and in any case, i don't understand why gmail is not having these problems.

It might be that berkeley.edu is blocking Fastmail. Further testing may help ascertain if this is correct.

[communicant]

Originally Posted by David

I deleted my earlier post botolo because it was not (strictly) correct. Creating a personality (of an account you own) though legal in the sense that it is not a forgery is in fact a dangerous one; you are sending mail from an SMTP server that is not the one of the account 'from address' - this is a dangerous tactic (especially for business email) imo.

Why do you say it is a "dangerous tactic"? Dangerous in what sense, and for whom? If it is done for convenience and to serve legitimate purposes and not for purposes of deception, then what is the problem?

[kaptitsky]

Spoofing a "from address," sending without authorization from the domain that owns that address, increases the possibility that other mail servers will reject or discard the mail as being forged.

Internet e-mail has never been a guaranteed delivery service. You have no guarantee that mail you send will get to the intended recipient.

In today's climate, though, sending mail with a spoofed or forged address offers more danger that it will not be delivered.

That's why Gmail always sent mail with the sender as being a Gmail (or Google Apps hosted) domain, even if the "from" address was different, leading to the "on behalf of" in Outlook.

Now, of course, they also offer sending through authenticated SMTP, for the same reason.

And one reason is to reduce the danger that mail will be rejected or discarded as being spoofed or forged.

[David]

Originally Posted by communicant

Why do you say it is a "dangerous tactic"? Dangerous in what sense, and for whom? If it is done for convenience and to serve legitimate purposes and not for purposes of deception, then what is the problem?

Blocking mail sent by an unathorized SMTP server is common practice these:

SPF "Sender Policy Framework" is an authentication solution to fight against email address forgery by checking the validity of the sending email server.

eg: checking that the sender is legitimate for the domain-name indicated in the "From:" field.

[elvey]

Originally Posted by botolo

and in any case, i don't understand why gmail is not having these problems.

Yes, this is disconcerting. But you are quick to blame fastmail. What is the domain part of your girlfriend's address? (The part to the right of the "@")

If fastmail fails to deliver a message to the receiving server, it always provides an error message. In this case, it seems very likely that berkeley.edu accepted the message and then discarded it.

[botolo]

Originally Posted by elvey

Yes, this is disconcerting. But you are quick to blame fastmail. What is the domain part of your girlfriend's address? (The part to the right of the "@")

If fastmail fails to deliver a message to the receiving server, it always provides an error message. In this case, it seems very likely that berkeley.edu accepted the message and then discarded it.

Fastmail replied to my support request and confirmed that the messages were bounced back from the recipient's server.

What I am saying is:

- I had no problem sending the same emails from the same from:address to the same recipients via gmail and me.com;

- Fastmail provided me with the error messages but these error messages were NEVER delivered to the mailbox.

The problem is the reliability of a service. While I know that Fastmail is a very good service, the fact that I had to realize by myself that messages were not being delivered is very bad. Can you imagine if my girlfriend kept on sending messages for several days? Lucky us that we realized it asap.

And you can imagine what my girlfriend said: "why did you move my account? you could have left it on gmail and I would not have had any problem".

[botolo]

Originally Posted by elvey

Yes, this is disconcerting. But you are quick to blame fastmail. What is the domain part of your girlfriend's address? (The part to the right of the "@")

If fastmail fails to deliver a message to the receiving server, it always provides an error message. In this case, it seems very likely that berkeley.edu accepted the message and then discarded it.

Forgot to answer your question. It's @berkeley.edu and she was sending emails to @berkeley.edu accounts.

[hadaso]

Originally Posted by botolo

Forgot to answer your question. It's @berkeley.edu and she was sending emails to @berkeley.edu accounts.

It's most likely that Berkeley's email servers have a policy to reject email from outside sources identifying as berkeley.edu.

They also publish an SPF record:

berkeley.edu    text =
    "v=spf1 ip4:128.32.61.96/27 ip4:169.229.218.128/25 ip6:2607:F140:0:1000:  :/64 ~all"

The "~all" in the end means that if the sending machine is not in the specified range then it is possible but not likely a legitimate sender. This is said to be even more dangerous than sending from a machine that is definitely excluded from the range because in the latter case servers using SPF would reject the message (producing a rejection message for the sender) and in the former case would accept the message and later silently discard it without notification, or file it in a spam folder that might not be checked by the user. So perhaps that professor received the email in his spam folder which he doesn't check? Some university email admins would set aggressive spam filtering thinking it's good practice (as "no spam is seen by the users. Who cares if they get the mail they want". They don't complain about wahat they do not know. They complain about spam all of the time).

Anyway, FastMail has a mechanism to avoid it: in the "Personalities" screen for the personality set to identify as "berkeley.edu" put her FastMail address (or alias, or subdomain address) in the "SMTP FROM Envelope" field and then it would pass SPF and probably other kinds of blocking (that's the way I managed to send email with my work address from my FastMail account to addresses within my employer's domain).

Something that worries me is the part about not getting rejection messages at her account, and then (you say) FastMAil staff said that FastMail received rejection messages. that's strange. Perhaps her account was set to discard them? Or perhaps they were sent to her berkeley.edu account which she doesn't check? (was it set to forward her email to where she reads it? perhaps it doesn't forward all email?)

[Bolman]

Originally Posted by hadaso

Anyway, FastMail has a mechanism to avoid it: in the "Personalities" screen for the personality set to identify as "berkeley.edu" put her FastMail address (or alias, or subdomain address) in the "SMTP FROM Envelope" field and then it would pass SPF and probably other kinds of blocking (that's the way I managed to send email with my work address from my FastMail account to addresses within my employer's domain).

I'm glad you mentioned that because it's a feature I didn't know about. SPF implementation several years ago has blocked me from using my office email address on Fastmail, but I checked out the "SMTP From Envelope" field, and it seems to work!

Thanks for a very useful tip!