Avoiding server blocking upon forwarding email to Gmail

[chrisjj]

I propose to set up my Fastmail to forward all mail to Gmail, but since this necessarily includes much of the kind of mail that Gmail has detects as unsolicited leading to it blocking the forwarding server, is there anything I can do to prevent the same befalling the Fastmail server? Sadly Gmail has no "trusted hosts" option.

Thanks.

[hadaso]

I have been forwarding email automatically to Gmail for several years. There's spam being forwarded (not all or even most of the spam I get) and it doesn't seem to have any effect on deliverability from FastMail to Gmail.

Gmail almost alway recognizes the spam correctly and files (labels) it under spam (it's not as good in avoiding ham being classified as spam).

[n5bb]

I agree with hadaso -- this isn't a problem. In my case, at Fastmail I target my Aliases and Virtual Aliases to the following (see this Fastmail blog post (item 2) for information about use of #noplus#):

fmusername+*@fastmaildomain,gmailusername+#noplus#@gmail.com

In the past month, 650 messages have accumulated in my Gmail Spam box, since address targeting bypasses the Fastmail spam and reject filters. And nearly 15,000 non-spam messages from my Fastmail account have been archived in this way at Gmail in the past 25 months.

In order to separate the retargeted Fastmail messages from messages sent directly to my Gmail account, I use the following filter in Gmail Settings>Filters:

• Matches: -{deliveredto:gmailusername@gmail.com}
  Do this: Skip Inbox, Mark as read, Apply label "Fastmail backup"
• Matches: deliveredto:gmailusername+sent@gmail.com
  Do this: Skip Inbox, Mark as read, Apply label "[Imap]/Sent"
• Matches: deliveredto:gmailusername@gmail.com
  Do this: Forward to (gmailalias at Fastmail)

I also created the Gmail label "Fastmail backup". And I have the label "[Imap]/Sent" (can't remember if I had to create it or if it was already there).

To get my messages sent from Fastmail into Gmail, I set up the main Fastmail personalities I use in this manner:

• BCC address(es): gmailusername+sent@gmail.com
• BCC on SMTP: checked

So with these changes in my Fastmail setup and Gmail setup, the following happens:

• Messages sent directly to my Gmail account arrive at my Gmail Inbox, and due to the third Gmail rule above are forwarded to the Gmail folder at my Fastmail account, so I can read them there.
• When any messages arrives at my Fastmail account (for aliases targeted as shown above), a copy of the message appears in my Gmail account with the Fastmail backup label, bypassing the Gmail Inbox and automatically marked as read. This bypasses the Fastmail spam filter (and all Fastmail rules), but the Gmail spam filter still works to file spam normally at Gmail.
• When I sent an email from either the Fastmail web interface or an email client which uses the mail.messagingengine.com SMTP server (using a Fastmail From Personality set as shown above), a copy of the sent message (marked as read) appears in my Gmail account in two places:
  • The Fastmail backup label (threaded with received messages)
  • The [Imap]/Sent label (only sent messages)
• So this allows me to see in Gmail fully threaded (received and sent messages) conversations I'm having through my Fastmail account!

Bill

[Berenburger]

Thank you Bill. As always, very informative. You're outstanding!

[chrisjj]

Originally Posted by n5bb

I agree with hadaso -- this isn't a problem.
In the past month, 650 messages have accumulated in my Gmail Spam box,

Thanks, but though I can well believe that 650 spams a month is not problem, here the rate is about 30,000 spams a month, causing Gmail eventually to respond

    SMTP error from remote mail server after end of data:
    host gmail-smtp-in.l.google.com [74.125.91.27]:
    550-5.7.1 [snip] Our system has detected an unusual rate of
    550-5.7.1 unsolicited mail originating from your IP address. To protect our
    550-5.7.1 users from spam, mail sent from your IP address has been blocked.
    550-5.7.1 Please visit http://www.google.com/mail/help/bulk_mail.html to review
    550 5.7.1 our Bulk Email Senders Guidelines. r20si7272894qcs.98

PS I find Gmail search is apparently inaccurate when used to find the spam rate e.g. in:spam after:2009/8/25 before:2011/8/26 reports 100 matches despite that I can see thousands.

[n5bb]

Originally Posted by chrisjj

Thanks, but though I can well believe that 650 spams a month is not problem, here the rate is about 30,000 spams a month, causing Gmail eventually to respond...

Wow! Are those all addressed directly to an alias at your Fastmail account, or are most of those addressed to some other service and forwarded to your Fastmail account? I get mail addressed directly to many aliases at Fastmail domains and my own (virtual) domain, and through forwarding from at least three other email services. But you are receiving nearly 50 times the raw spam as me (before the Fastmail spam filter).

Fastmail can block insecure email sources if they are addressed directly to your Fastmail account (either through Fastmail aliases or virtual domain aliases at your personal domains). But I don't believe this will reliably block insecure senders sending through email forwarding services.

Bill

[chrisjj]

Originally Posted by n5bb

or are most of those addressed to some other service and forwarded to your Fastmail account?

Yes.

(some more characters to satisfy the forum posting form.)

[flinchlock]

(Yes, I know this is a very old post.)

Originally Posted by n5bb

In my case, at Fastmail I target my Aliases and Virtual Aliases to
<snip>
So this allows me to see in Gmail fully threaded (received and sent messages) conversations I'm having through my Fastmail account!

I am in the process of also using Gmail as a CYA Backup. Are you still using this setup?

THANKS,
Mike

[n5bb]

Originally Posted by flinchlock

I am in the process of also using Gmail as a CYA Backup. Are you still using this setup?

Mike, I stopped forwarding to Gmail last week. I decided that I didn't want Google knowing everything about me, and Fastmail has never lost a single message in the 8 years I have had an account. Fastmail also has a new beta threaded interface. But if you want to use my method, it worked well.

Bill

[flinchlock]

Bill,

Thanks. The new interface looks very good! Is there a place to report problems on this interface?

And nearly 15,000 non-spam messages from my Fastmail account have been archived in this way at Gmail in the past 25 months.

Do/did you keep these messages on FM, or some other site?

THANKS,
Mike

[n5bb]

Mike, there is a thread at EMD Forums concerning the new beta AJAX interface. It is beta, so many things are broken and so there isn't really a need yet to report every bug.

I keep all of my email on the Fastmail server. I have an Enhanced account so I'm only using 26% of my 10 GB mailbox quota right now. From time to time I use IMAPsize and/or Thunderbird to make local copies on a PC. Fastmail no longer has a monthly transfer quota (just short-term limits), so I don't need to worry about transfer problems for such a large mailbox. IMAPsize can make incremental backups to your local PC. The latest IMAPsize version is 0.3.7, and it is freeware (donations to the author are accepted at the site).

Bill

[lane]

Originally Posted by n5bb

Mike, I stopped forwarding to Gmail last week. I decided that I didn't want Google knowing everything about me, and Fastmail has never lost a single message in the 8 years I have had an account. Fastmail also has a new beta threaded interface. But if you want to use my method, it worked well.

Sounds as though the new privacy bundle is the last straw for you. I have also been having increasing misgivings, though I have not yet pulled the plug.

Of course you could back up at another email host instead of Gmail, using pretty much the same procedure. For example, Tuffmail, Polarismail, Yahoo etc. But not Hotmail (my recommendation); they do not, or at least did not in the past, handle forwarded mail very well with regards to spam.

[chrisjj]

Originally Posted by n5bb

Fastmail has never lost a single message in the 8 years I have had an account.

Out of interest, how do you know?

[n5bb]

Originally Posted by chrisjj

Out of interest, how do you know?

Here is what I have experienced -- note that these are my feelings, and others may think differently. There is no way to know for sure that every single message is still stored in the Fastmail message store.

• I have never been told by someone that they sent me a message but I never received it. This is true for commercial and personal senders.
• I have never missed an automated report from a company which I knew should have been sent (such as a weekly update email).
• All messages I ever remember receiving (or which others ask me about) which I'm sure I didn't delete are still visible in my account. This is an imperfect measure, but it's my gut feel.
• In my 8 years of using Fastmail, there has never been an instance when they reported a loss which affected me. There have been delivery delays, but this is not loss.

Bill