Outlook 2011 / Lion

Discussion in 'Mac Apps and Mac App Store' started by macheed, Nov 23, 2011.

  1. macheed macrumors newbie

    Feb 10, 2011
    Hi there,
    For a few weeks now I have been having a very annoying problem with my macbook pro.
    This problem happened just after I upgraded to Lion 10.7.2. Unfortunately, at the same time my ISP also 'upgraded' their email system.
    Since then, Outlook 2011, often is unable to send emails, it retrieves them all okay but then comes up with a 'temporary error' when it tries to send emails. It does eventually manage to send them okay but only after a few attempts which is very annoying when you are trying to get an email to go quickly.
    Does anyone else have this kind of problem?
  2. Macman45 macrumors G5


    Jul 29, 2011
    Somewhere Back In The Long Ago
    You Are Not Alone

    Outlook for Mac is full of holes, I ditched it in favour of Thunderbird. Check out the MS support pages for office on mac....Its a horror story.
  3. dianeoforegon macrumors 6502a


    Apr 26, 2011
    Without knowing what type of account? (POP, IMAP, Exchange) it's hard to offer suggestions.

    BTW, are you upgraded to 14.1.3?

    BASICS Send & Receive

    1. If you can receive but not send then you have a bad SMTP configuration
    2. If you can send but not receive you have a bad POP or IMAP configuration

    Check under advanced settings. Check your provider's website for exact info on authentication, SSL and ports. It's not uncommon for them to update and either not send out notices or the notice ends up in junk and you didn't see it.

    Some ISPs require SSL for receiving
    Most ISPs require advanced settings now for SMTP
  4. macheed thread starter macrumors newbie

    Feb 10, 2011
    Thank you for your replies which are greatly appreciated.
    Diane, I have actually gone through all the set up info with my ISP Tech Support and it is all set up correctly. However, it still fails to send emails about 4 out of 5 attempts which is very annoying. The thing is, if something was set up wrongly, it would probably never work so I am a but puzzled about how it works sometimes. Outlook has been upgraded to 14.1.3 and Lion to 10.7.2.
    The very weird thing is this - I set up a parallel account on Mac Mail - same ISP settings etc. but just a different email address using the same account. Mail also sometimes has the same sending problem. It reports 'Cannot send message using the server Outgoing email server'. However, after a few tries, it gets to send the message okay.
    The weirdest thing is this - if Outlook tries to send an email and fails, then I also open up Mail and do nothing other than opening it up, Outlook will then be able to send the email! - weird or what!
    I simply cannot work out if the problem is on my Mac/Outlook/Mail or if it on the ISP side of things.
  5. MisterMe macrumors G4


    Jul 17, 2002
    I notice that you are using a MacBook Pro. Despite having been asked, you have given zero (0) information about your ISP or the type of email account at issue. Lacking evidence to the contrary, I will go out on a limb and say that you have problems sending email when you are outside your ISP's domain. This is not a problem; it is a standard security feature.

    Again, lacking evidence to the contrary. I will assume that you have a POP3 account. Your outgoing mail server is a SMTP server. Your SMTP server uses Port 25 for unauthenticated access when you access the Internet through your ISP. Other providers often block access to your SMTP server when you access the Internet away from home. There is a workaround, Authenticated SMTP. The standard port for authenticated SMTP access is Port 587. Port 587 requires your username and password. Port 25 requires neither. You should change your SMTP port to 587 because Authenticated SMTP works inside and outside your ISP's domain.
  6. macheed thread starter macrumors newbie

    Feb 10, 2011
    Hi MisterMe,
    Thank you very much for your suggestions and help and sorry for not giving you more information to go on.
    It is a pop3 email account and the isp is a UK-based one which used to be called force9.net but was rebranded to plus.net a few years ago. However, legacy users like me still use the force9 information to get onto their system.
    I have just tried implementing the changes that you suggested and I am afraid that they also did not work. Your deductions were excellent but, unfortunately, email sending does not work whether I am within the ISP's domain or not.
    I now strongly suspect that the problem lies at the ISP's end as I have now changed the sending email information to a GoDaddy account which I also have and that works reliably.
    Any other thoughts or ideas would be much appreciated.
    Thanks everyone.
  7. dianeoforegon macrumors 6502a


    Apr 26, 2011
    You can use Eavesdrop to monitor your connection. Eavesdrop is an application for listening in on TCP conversations on the network your computer is attached to.

    Another option is to use tcpflow to monitor traffic. more info

    This might give you clue to what is failing.

    Getting a new ISP might be your best option. :)


    If it's an on/off issue, the problem is most likely with your provider and not your email client.

    You can verify by entering the account in Apple Mail and see if you see the same issue.

    If Apple Mail gets all the mail on a timely basis, then Outlook is to blame.
    If you see the same behavior in Mail, the problem is with your server.

    Also note your location could be a factor in sending.

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