Office 365 Sign-In Changes

Coming in March 2013, following the release of the next version of Office 365, users will be presented with a streamlined sign-in experience. The sign-in page will a feature responsive design and was designed to “provide the best possible performance and experience on computing devices”.

Office 365 Responsive Sign-In

If you’d like to opt-in earlier and test drive the new experience, click here.

Post opt-in, here’s what you’ll experience on the desktop.

Office 365 Updated Sign-In

Apostrophes in Email Addresses with Exchange Online (Office 365)

There are several characters that can come off your keyboard that can make life with Office 365 a little painful, especially in a coexistence scenario. One such pain point is the use of special characters like an apostrophe (‘) in user principle names and email addresses. Please note that it is not possible to utilize an alias with an apostrophe in a non-coexistence scenario as the Exchange Online administration screens will not allow you to create the alias with illegal characters.

If you have any users like this in your environment, the first step is to transition them over to a user name that does not make use of an apostrophe (or any other illegal characters) and also ensure that their primary email address (under the Proxy-Addresses attribute in Active Directory) does not contain any illegal characters as well. If your users have illegal characters in their user name, they will experience errors similar to those found in KB2439357 - Error message when you try to create a user name that contains a special character in Office 365: “Invalid user name”.

After the user has been properly configured, they will be able to send and receive messages via an alias that contains an apostrophe.

Office 365 Character Matrix

The following table details the special characters and their usage scenarios in Office 365 for user names, passwords, and email addresses (see Characters in passwords or user names in Office 365 for the original. I’ve added the email address column here).

Character Name Character Allowed In
User Name Password Email Address
Accent ` No Yes No
Ampersand & No Yes No
Angle Brackets < > No Yes No
Apostrophe No Yes Yes***
Asterisk * No Yes No
At Symbol @ No Yes No
Backslash \ No Yes No
Braces [ ] No Yes No
Brackets { } No Yes No
Circumflex ^ No Yes No
Colon : No Yes No
Comma , No Yes No
Dollar Sign $ No Yes No
Equal Sign = No Yes No
Exclamation Point ! No Yes No
Hyphen - Yes* Yes Yes*
Number Sign # No Yes No
Parentheses ( ) No Yes No
Percent Symbol % No Yes No
Period . Yes* Yes Yes*
Pipe | No Yes No
Plus Sign + No Yes No
Question Mark ? No Yes No
Quotation Mark No Yes No
Semicolon : No Yes No
Forward Slash / No Yes No
Tilde ~ No Yes No
Underscore _ Yes** Yes Yes**
Uppercase Letters (A-Z) A-Z Yes Yes Yes
Lowercase Letters (a-z) a-z Yes Yes Yes
Numerals (0-9) 0-9 Yes Yes Yes

* You can put a period or hyphen anywhere in your user name or email address except at the very beginning or at the very end.
** You can put an underscore anywhere in your user name, including at the very beginning or at the very end.
*** Apostrophes can be used in non-primary email addresses (aliases) for both receiving and sending messages.

Configuring the Alias

Any user who wishes to make use of an email address with an apostrophe will need the additional addresses created within the source domain. A domain administrator or user with rights to update the Proxy-Addresses attribute within Active Directory should add the applicable aliases on behalf of the user.

For instance, if the user Demo O’Reilly (UPN wishes to have an additional alias provisioned for the address demo.o’, an additional proxy address of smtp:demo.o’ should be applied to the user’s account in Active Directory. After the applicable proxy addresses have been applied, a Directory Synchronization (DirSync) should occur (either manually initiated or on the existing schedule) before the email address will be available for use in Exchange Online. After DirSync has completed, an Office 365 Exchange Administrator can verify that the alias has been applied to the user’s federated account.

Testing the Alias

After an Office 365 Exchange Administrator has verified that the alias has been created successfully, a test message should be sent to the user to verify that messages are being routed as intended. Note that the messages will be routed to the users primary email address (e.g.

Configuring Outlook to use the Alias

This is where the magic happens. As Outlook Web Access does not support multiple “From” accounts, we need to configure a 3rd-party client (in this case Outlook) to allow our user to send messages using their new alias. We’re going to be using the directions found at How to add an alias to an Office 365 account and how to set up Outlook to send email messages as this alias.

  • Retrieving Outlook Configuration Settings
    1. Sign in to the Office 365 portal, and then in the header, click Outlook.
    2. Click Options, and then click See All Options.
    3. In the left navigation pane, click Account, and then click My Account. Under Account Information, click Settings for POP, IMAP, and SMTP access.
    4. The Protocol Settings window lists the POP, IMAP, and SMTP settings for the user. Keep this window open or copy the settings information. You will need the information in the next step.
  • Configuring Outlook to Send Messages as the Alias
    1. Open Outlook with the Office 365 profile.
    2. Click File, then click Account Settings, and then click Account Settings.
    3. On the E-mail tab, click New.
    4. Click Manually configure server settings or additional server types, and then click Next.
    5. Click Internet E-mail, and then click Next.
    6. Enter the following information:
      • Your name: The user’s display name
      • E-mail Address: The alias that you want to send from.
      • Account Type: POP3
      • Incoming mail server: Use the POP setting that you obtained in Step 1. It should resemble
      • Outgoing mail server (SMTP): Use the SMTP settings that you obtained from Step 1. It should be the same or similar to the POP3 setting.
      • User name: The user’s Office 365 sign-in name/email address.
      • Password: The user’s Office 365 password.
    7. Click More Settings.
    8. Click the Outgoing Server tab, and then click to select the My outgoing server (SMTP) requires authentication check box.
    9. Click the Advanced tab, and then click to select the This server requires an encrypted connection (SSL) check box.
    10. In the Outgoing server (SMTP) box, type 587.
    11. In the Use the following type of encrypted connection list, click TLS.
    12. Under Delivery, set the delivery options that you want.
    13. Click OK.
    14. Click Next. The account settings that you entered are tested. When these tests are completed, click Close.
    15. Click Finish.

    A POP3 account is created for the alias. However, you also have to make sure that this POP3 account does not send and receive items in Outlook.
  • Making Sure the POP3 Account Does Not Send/Receive Items
    1. In Outlook, click File, click Options, and then in the left navigation pane of the Outlook Options window, click Advanced.
    2. Under Send and receive, click Send/Receive.
    3. In the Group Name area, select All Accounts, and then click Edit.
    4. In the Accounts list, select the new email alias account.
    5. Click to clear the Include the selected account in this group check box.
    6. Click OK, click Close, and then click OK.
  • Enable the From Field in Outlook
    To change whom the email messages are sent from (either from the user’s aliases or primary address), you may have to enable the From field in Outlook. To do this, follow these steps:
    1. In Outlook, click New E-mail to open a new email message.
    2. Click the Options tab. In the Show Fields group, click From to enable the From field in all new email messages.
  • Verify The Alias Can Send Messages in Outlook
    Send an email through the now configured “dummy” POP account to verify that messages are being routed as expected.