Fixes or workarounds for recent issues on Outlook.com

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When you try to send an email from a device running iOS 11, you might see this error message: "Cannot Send Mail. The message was rejected by the server." This affects email from Outlook.com, Office 365, or an Exchange Server 2016 running on Windows Server 2016.

Apple is working closely with Microsoft to resolve the issue and will release a fix soon in an upcoming software update.

Until then, customers can download the free Outlook for iOS app or go directly to Outlook.com.

ISSUE

After connecting to Outlook for Windows (Outlook 2016, 2013, 2010 versions) to your Outlook.com email account, your may experience the following:

• Your email account name shows up as outlook_[long series of letters and numbers]@outlook.com in the Folder Pane and when composing emails using Outlook for Windows.

• Recipients will also receive the email from the sender with the outlook_[long series of letters and numbers]@outlook.com format.

• When recipients reply to the email, the email bounces and you may receive the message “Undeliverable message when you send Internet mail in Outlook.”

This issue only impacts customers using Outlook for Windows. Emails sent via Outlook.com on the web works correctly and emails will be sent with the correct email address.

WORKAROUND

This issue occurs for users with multiple account aliases. We are actively working on a fix. In the meantime, to fix this issue, please do the following:

1. Go to https://account.live.com/names/Manage and sign in to your Outlook.com account.

2. Set your Outlook.com email as the primary alias.

3. In Outlook for Windows, remove and re-add the account. See the steps in this article: Add your Outlook.com account in Outlook for Windows

Last updated: February 8, 2017

ISSUE

If Outlook is connected to a primary Outlook.com account that is also connected to other secondary non-Microsoft accounts (such as Gmail, Yahoo, etc.), when sending an email in Outlook, you are not able to choose the other secondary connected account as the "From" sending account.

If you manually type in the secondary connected account email address in the "From" field, the email is sent as "On behalf of" your primary Outlook.com account.

STATUS: WORKAROUND

Outlook supports sending from a secondary connected account for Microsoft owned domains such as @outlook.com, @live.com, @hotmail.com but has not implemented this functionality for third-party domains.

The Outlook team is listening to your feedback and investigating adding this functionality to future updates. Please vote up the request and add any feedback on UserVoice: Option to make Microsoft Outlook 2016 work with Outlook.com connected. In the meantime, please use the following workaround:

WORKAROUND

You can also add the secondary connected accounts (Gmail, Yahoo, etc.) in Outlook.com as additional accounts in the Outlook profile.

1. In Outlook, choose the File tab.

   

2. Under Account Information, choose Add Account.

   

3. On the Auto Account Setup page, enter your name, email address, and password, and then choose Next.

   Note: If you receive an error message after choosing Next, double check your email address and password. If both are correct, see the next section.

4. Choose Finish.

For more information, please see Outlook email setup.

Last updated: May 2, 2017

Currently, you can't use Outlook on Windows to edit calendars that are shared with your Outlook.com account, even if you've reconnected your Outlook.com account to Outlook. We're working to make it possible to edit shared calendars in Outlook 2016 for Windows.

To edit a shared calendar, go online to your own Outlook.com calendar, open Calendar for Windows 10, or use a mobile device. Read how to Add your Outlook.com account to another mail app.

Last updated: May 2, 2017

ISSUE

When you try to accept a shared Outlook.com calendar using your Office 365 for business account in Outlook 2016, you might receive the "Something went wrong" error or your sign-in might fail.

STATUS: WORKAROUND

To access the calendar shared with your Office 365 for business account, you’ll need to accept the invitation from Outlook on the web . If you've already clicked the Accept button in Outlook 2016, you won't be able to re-accept the invitation in Outlook on the web. The person who sent you the invitation will need to remove your permissions and then send a new invitation.