I have troubles accessing Gmail account from Outlook.

galanda91 · Jul 25, 2019, 8:54 PM

I already configured firewalls rules to permit the traffic from my network to gmail servers, I'm using squid proxy server. I created a ACLs to permit the traffic in imap and smtp ports. If I connect the computer in other free network gmail works good, but into the proxy network don't. Please I someone can help me!

Re: Nao consigo liberar imap.gmail.com

kiokoman · Jul 25, 2019, 9:16 PM

this is the same answer that marcelloc gave in that post

squid only filter traffic HTTP(s).
there is no way that it can block imap/pop3/smtp, there must be something else.
squid is not a proxy for mails, if you have manually configured the proxy on your mail client (outlook/thunderbird) that is wrong

KOM · Jul 26, 2019, 4:31 PM

Unless Outlook is using tcp80,443 to access gmail then squid has nothing to do with it. I don't know Outlook well enough to know how it accesses gmail, but I would guess it's using the standard imap/s ports. To find out, check squid's access logs to see if it's blocking anything when you try to fetch your mail. Otherwise, check your firewall log to see if it's blocking anything.

Are you running any packages like pfBlocker or any other package that might interfere with LAN traffic?

kiokoman · Jul 26, 2019, 8:54 AM

i can assure you that outlook use standard pop3/imap port if you are not using MAPI over HTTP for exchange

galanda91 · Jul 26, 2019, 4:22 PM

@kiokoman Thanks!

I suspected that, but I can't understand the problem. Because if I connect directly to the LAN port of the psfense I can synchronize outlook, but if I connect from my internal network it not works but I can surf in internet thought pfsense pxoxy ok.

galanda91 · Jul 26, 2019, 4:31 PM

@KOM Thanks!

I'm using these cnfiguration:

imap.gmail.com : 993

smtp.gmail.com: 465

*.gmail.com, imap.gmail.com, smtp.gmail.com, gmail-smtp-msa.l.google.com and gmail-imap.l.google.com

I checked squid's access logs and firewall log but I didn't see anything. the network is using pfsense like a proxy only (not like a firewall).

I'm not running any packages lthat mignt interfere with LAN traffic. I only have squids packages.

KOM · Jul 26, 2019, 5:34 PM

Well, squid doesn't pay attention to ports other than tcp80,443 unless you manually add them, so it's not the problem.

With gmail, isn't there a trusted applications feature that you must explicitly allow apps to use the account or something like that?

Benjam7 · Aug 20, 2019, 6:15 AM

@galanda91 said in I have troubles accessing Gmail account from Outlook.:

@KOM Thanks!

I'm using these cnfiguration:

imap.gmail.com : 993

smtp.gmail.com: 465

*.gmail.com, imap.gmail.com, smtp.gmail.com, gmail-smtp-msa.l.google.com and gmail-imap.l.google.com FirstPremierCard

I checked squid's access logs and firewall log but I didn't see anything. the network is using pfsense like a proxy only (not like a firewall).

I'm not running any packages lthat mignt interfere with LAN traffic. I only have squids packages.

I don't know Outlook well enough to know how it accesses gmail, but I would guess it's using the standard imap/s ports. To find out, check squid's access logs to see if it's blocking anything when you try to fetch your mail. Otherwise, check your firewall log to see if it's blocking anything.

bmeeks · Aug 20, 2019, 9:53 PM

Have you checked out this thread from Microsoft Support?

https://support.office.com/en-us/article/import-gmail-to-outlook-20fdb8f2-fed8-4b14-baf0-bf04b9c44bf7

It walks you through the steps. As @KOM mentioned, you must first configure your Gmail account to create an application password that Outlook will then use for access to Gmail. All the steps are in the link I posted.

I use my Gmail account with Outlook 365.