I don't believe I've done anything wrong lately to cause this dilemma. Can anyone offer some assistance? It will be greatly appreciated. As stated before, all this means is your outgoing server credentials are incorrect in the Mail App.


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Click on your gmail account then under "outgoing server" check what server is chosen by default then click "edit smtp server list" at bottom. Once there double check all the server info. Make sure it has your email spelled correct and password correct, make sure authentication is set to "password" then make sure you use SSL and use port or I had the same problem.

All my settings seemed correct. Basically, you skipped the authentication step when setting up the outgoing emails, so you're sending an email that connects to a server with no credentials, hence the "unable to send" message. Hope this helps someone who is new to Mac OS! I have also gotten this error recently and the fix is simple. I am not exactly sure where, but somewhere in the mail app probably in the preferences there is a setting to change which outgoing mailbox it uses.

When it happened to me it was set to an "offline" mailbox and all I had to do was change it to an "online" one.

If Mail refers to a problem with the mail server or network

Restarting the mail app may be necessary. Encountered this issue also after enabling the 2 step verification. Resolution was to generate a new app specific password for Mail on Mac and added it back to the Outgoing server settings. It appears this issue was fixed in I have been having the same issue for 6 months and was unable to fix it despite trying all of things that I had read.

On all my other devices, even though I have not changed any of the settings , in mid-September Hotmail started to behave as if it were set up for IMAP. I had left my laptop open and gone out with my iPhone. Normally I would have to mark all messages as read on my phone even if they had been seen on my laptop. Now, however, as soon as the laptop recognises the email has been seen it automatically marks it as read on my mobile.

How to Configure Outlook Windows Live MSN Hotmail IMAP in Apple Mail on Mac OS X

Even if you change the server hostname, which it will let you do, the problem will still persist. The only way to do this it seems is to actually delete the hotmail account completely from Mac Mail but this means that you lose all your emails over however many years you have had the account. Step 1 — Export all your emails. Mac Mail has a nifty feature which allows you to export all of your emails in one go. Before you do this though you need to make sure it selects all of your emails. I thought that if I did this it would simply lift everything as long as I had highlighted the correct mailbox account on the left hand side but the first time I tried I only got a partial copy.

Step 2 — Disconnect your Hotmail account from iCloud.

hotmail and Mac Mail - Apple Community

This step only applies if you have used your Hotmail account as your Apple id. If you are unsure then try this next bit anyway as the system will tell you whether you are linked or not.


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  8. Click on the minus sign to remove the account and if you are linked you will see a pop up dialogue box. Follow the link to preferences and then unlink your email from iCloud. It will offer you the choice of keeping the data on your Mac or deleting it as you go; the choice is yours but I chose to delete everything. Step 3 — Add a new email account onto your Mac Mail. Now just add your Hotmail back in. When it does this you will see straight away that is defaults to IMAP and the settings it uses are those on the Apple Mail Settings lookup. When it has finished it will probably bring in the last couple of weeks of emails from your Hotmail account and you will now have a fully functioning Hotmail account back on your Mac.

    Choose the file from your desktop or wherever you saved it and OK that. You now have a working Hotmail account on your Mac and all your old emails available when you need them. If you are still getting problems then feel free to comment below! I have the problem that Hotmail setup as imap on my Yosemete based Air has been working fine until a few days ago, then it just stopped. I deleted and re-added it, but that did not work. That I would imagine is what happened to you.

    I think you are right. I have done this step at least 5 times already, and my hotmail account is still not working, it keeps asking me for the password every 5 seconds, the password is correct and none of the other solutions works for me. This guide contains the settings and instructions how to configure Outlook with those email providers. The settings below are sorted by the dialogs that you need to access.

    If you can’t send or receive email on your Mac

    If you are having problems finding out where to put in which information, look at the numbers in front of the settings and you can find them back in the screenshots section at the bottom of this document. When you are using the Mail app on your smartphone or tablet, you can configure your Outlook. Connecting to your Outlook. In Outlook, simply select to add an account and use the Auto Account Setup method to configure your account. Manual configuration of the servers is not needed nor supported.

    To manually configure your Outlook. More Settings: Outgoing Server tab screenshot. The Outlook Hotmail Connector is no longer supported nor needed to connect to your Outlook. IMAP should already be enabled by default for all accounts.

    Outlook.com (Hotmail)

    For more information and workarounds see: Gmail accounts and disproportionally large pst-files. Office also offers EAS connectivity but that is only recommended for mobile devices such as smartphones and tablets which are using an Outlook app or another Mail app which offers EAS support. IMAP and POP3 is also offered but that is only recommended when you have a very specific need for it like server-level automation or not using Outlook.

    Question Info

    Connecting to your Exchange Online mailbox is really easy as Outlook makes use of the Autodiscover service to automatically configure Outlook. Manual configuration is not supported. Note to domain owners: Make sure that you have set all the required DNS records for your domain.