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Information Technology

Outlook Email and Calendar FAQs

How do I encrypt or send a secure email?
You can send an encrypted email to anyone in the world including any attachments to the email.  This can be accomplished by prepending the subject line of your email with the word “Secure: ” (please note the space after the colon) or by clicking the “Protect” button while composing a new message in Outlook on the web, located on  Some recipients may need to go through a one-time, brief Microsoft sign-up process to access your secure email.

Why can't I download my email attachments right away?
Your email attachments will automatically be scanned for malicious content such as viruses and malware.  As a result of this scanning, attachments are replaced with a placeholder file until scanning is complete and then reattaches the attachments if no malware is detected.  Microsoft Office documents and PDF attachments can be previewed while it is being scanned.  As a result, you may experience some minor delays when receiving emails with attachments.

What is the purpose of the "Focused Inbox" in Outlook?
"Focused Inbox" helps you focus on the emails that matter most to you. It separates your inbox into two tabs-"Focused" and "Other." Your most important emails are on the "Focused" tab while the rest remain easily accessible-but out of the way-on the "Other" tab. You’ll be informed about email flowing to "Other", and you can switch between tabs at any time to take a quick look.  Please visit "Turn off Focused Inbox" for detailed instructions for turning focus off.

How do I add a signature to Office 365 Outlook on the Web?
Follow this link for instructions.

How do I set up an "Out of Office" response?
Follow these instructions to set up an automatic reply.

How do I spellcheck in Outlook webmail?
In Office 365 Outlook on the web - there is no built-in spellcheck. Instead, use your web browser for spellcheck. Most web browsers such as Chrome, Internet Explorer, and FireFox have spellcheck.
If you're using Windows 8 or later, another option is to go to your PC Settings and search for Autocorrect misspelled words and Highlight misspelled words. Turn on both of these.

How do I open a shared mailbox in Outlook on the web?
Method 1: Open a Shared Mailbox using the Office 365 Portal (one-time)
1. Log into Office 365 by navigating to
2. Log in with your credentials
3. Access the "Mail" section by clicking the waffle icon (upper left) and clicking the "Mail" tile.
4. Click your user icon (upper right) and select the option "Open another mailbox..."
5. Enter name (or first few letters of the mailbox) in the mailbox field, select the mailbox, and click "Open".

Method 2: Add a Shared Mailbox to your View in Office 365 (persistent)
1. Log into Office 365 OWA by navigating to
2. Log in with your credentials
3. Access the "Mail" section by clicking the waffle icon (upper left) and clicking the "Mail" tile
4. Go to the left navigation pane
5. Under folders click "More"
6. Right click on your name
7. Click "Add shared folder"
8. Enter the email address of the shared mailbox (e.g.
9. Click Add

How can I block a specific email address?
From Outlook on the web, right click the email message and choose "Mark as Junk".

How long will messages remain in Deleted Items and Junk Email folders?
Items that are in "Deleted Items" or "Junk Mail" folders are purged from accounts after 30 days.

If I delete a message from my Outlook mailbox, can I recover the message?
Items remain in your deleted mail folder for 30 days and are recoverable for an additional 30 days. For assistance, please visit "How to recover deleted items or mail in Outlook"

How should I handle Junk email?
Office 365 will automatically flag some email as "Junk" and put it in the "Junk" folder. You should periodically review the items in the "Junk" folder to make sure no legitimate email was accidentally flagged.
Items in the "Junk" folder will be automatically deleted after they are 30 days old.

To mark email as "Junk" and help to train Office 365, do the following:

  1. Right-click the message
  2. Select "Mark as Junk"

To mark "Junk" email as legitimate, do the following:

  1. Right-click the message
  2. Select "Mark as Not Junk"

Are there any unsupported file types for attachments?
File attachments for security and compatibility reasons, files of some types and sizes cannot traverse the Office 365 e-mail system. Prohibited Files Types include: .ade, .adp, .bat, .chm, .cmd, .com, .cpl, .exe, .hta, .ins, .isp, .jse, .lib, .lnk, .mde, .msc, .msp, .mst, .pif, .scr, .sct, .shb, .sys, .vb, .vbe, .vbs, .vxd, .wsc, .wsf, .wsh Size Limits Office 365 has a maximum per message size limit of 25 MB (our previous limit was 10MB)

Can I use Outlook to access my Gmail account?
Yes, but this is a "self-service" effort.  Follow the directions, here.

How do I forward my email to a different email account?

  1. Go to
  2. Login with your Bentley email address and password.
  3. Click the Gear icon in the upper right.
  4. Under Your App Settings click Mail.
  5. Under Accounts Choose Forwarding.
  6. Enter the email account you wish to forward your Bentley mail to.
  7. Check Keep a copy of your forwarding messages if you wish to keep a copy of your forwarded mail.
  8. Click Save.

What should I do with email that comes from

View and Manage your Quarantined Mail

At the end of each work-day, you may receive an email from which contains a list of the suspect spam messages.  When you open this email, you have the option to:

1.  Release the message to your inbox if it is a legitimate message.  This will send the message to your inbox and remove it from quarantine, after which point you can interact with the message as you would any other.
2.  Report the message as "Not Junk".  The spam team evaluates and analyzes the message, and, depending on the results of the analysis, adjusts the anti-spam filter rules to allow the message through.  You can only release a particular message and report it as a false positive (not junk) once.
3.  Do nothing. If you choose to do nothing, the message will be deleted by Office 365 automatically upon expiration. By default, spam, bulk, and phishing messages are kept in quarantine for 15 days. A quarantined message that matches a mail flow rule is kept in quarantine for 7 days (you can't customize this). When Office 365 deletes a message from quarantine, you can't get it back.

Can I retrieve a message from quarantine before I receive the daily quarantine notification?
Yes.  You can view your quarantined messages at any time.  Open your web browser and go to  Log in with your Bentley University credentials.  After login you will see a listing of any messages destined for your inbox that have been quarantined because they are believed to possible be spam, junk, or phishing messages.  Once you click on a message in the list you can review it and decide whether the message should be sent to your inbox or not.  If you are not certain about how to deal with a particular message, feel free to contact the service desk.