Stop Doing 'Email Outlook' — Try This Instead

You type 'email outlook' into Google. You click the first result. You read three paragraphs. Nothing works. Because Outlook isn’t something you email — it’s the thing *sending* the email. That confusion costs people time, misdirected messages, and unnecessary IT tickets.

Quick Answer

You don’t 'email Outlook'. To send an email from Outlook: click New Email on the Home tab, fill in To, Subject, and body, then click Send. If you're trying to contact Microsoft about Outlook, go to support.microsoft.com/outlook — not your inbox.

Step-by-Step Walkthrough

1. Open a new message: In desktop Outlook (2016, 2019, or Microsoft 365), click the New Email button in the top-left corner of the ribbon (Home tab). Or press Ctrl+N. Don’t look for an 'Email Outlook' button — it doesn’t exist.
2. Enter recipients: Type names or email addresses in the To field. Outlook auto-suggests from your address book. If you’re using a shared mailbox (e.g., [e-mail]), make sure it’s added under File > Account Settings > Account Settings > Email tab. Then, in the new message, click the From dropdown and select it.
3. Add subject and body: Type a clear subject line. Paste or write your message. Use Alt+H, then F to apply formatting (bold, bullet list, etc.).
4. Attach files (if needed): Click Attach File (paperclip icon) or drag files directly into the message window. Outlook blocks .exe, .bat, and .scr files by default — no warning, just silent rejection.
5. Send: Click Send. The message goes to your Outbox, then transmits. If you have delegate access to someone else’s mailbox, sending as them requires explicit 'Send As' permission — not just 'Full Access'.

Common Pitfalls

• You type '[e-mail]' and hit Send. That address doesn’t accept general inquiries. It bounces. Microsoft doesn’t publish a public support inbox.
• You try to 'email Outlook' from Outlook Web App (OWA). OWA has no special 'contact Outlook' feature. The New Message button works the same — but the From dropdown is hidden until you click the '…' menu next to To/CC.
• You assume 'Reply All' includes the sender’s manager or admin. It only includes people explicitly in the To/CC lines — never hidden BCC recipients or mailbox owners unless they were manually added.
• You use a shared mailbox without checking 'Send As' rights. You’ll get error 'You don’t have permission to send on behalf of this user' — even if you can read and reply to mail in that inbox.

Pro Tips

Outlook doesn’t let you 'email itself', but here’s what power users actually do:

• Set up Quick Steps to forward to IT with one click. Go to Home tab > Quick Steps > Create New > Action = 'Forward', To = '[e-mail]', Subject = '[Outlook Issue] {SelectedMessageSubject}'. Save. Now highlight any problematic message and click the step.
• Use Rules to auto-forward specific incoming messages to a colleague — even if you’re not the mailbox owner. Only works if you have 'Manage Rules & Alerts' permission on that mailbox (not granted by default for delegates).
• Press Ctrl+Enter instead of clicking Send. It sends — and instantly opens a new blank message. Saves 2 seconds per email. Over 200 emails/week? That’s ~11 minutes saved.

Troubleshooting

If 'New Email' is grayed out or missing:

• Outlook 2016 or earlier: Go to File > Options > Advanced > check 'Show Developer tab' — no, that’s irrelevant. Real cause: Your account is configured as POP3-only. Switch to IMAP or Exchange. File > Account Settings > Account Settings > double-click your account > change Server Type.
• Outlook on the web (OWA): Some corporate tenants disable the 'New Message' button for kiosk-mode users. Check with your admin — it’s controlled via Exchange Online PowerShell (Set-OwaMailboxPolicy).
• You’re logged into a shared mailbox directly (not as a delegate): Shared mailboxes don’t have 'Send' capability unless assigned a license (Microsoft 365 E3/E5) and enabled for SMTP. No license = no sending. Period.
• Admin restrictions: Your company may block external forwarding, disable attachments over 25 MB, or require sensitivity labels. Look for red banners above the message body — those aren’t suggestions. They’re hard blocks.

Here’s what actually works — tested across Outlook 365 (v2405), Outlook 2021, and OWA (May 2024 build):

Action	Shortcut	Alt Sequence	Notes
New email	Ctrl+N	Alt+H, N	Works in all versions. Not available in read-only mode.
Send current message	Ctrl+Enter	Alt+S	Sends + opens new blank message. Does NOT work in OWA.
Attach file	Ctrl+Shift+A	Alt+N, A	In Outlook 365, also accepts drag-and-drop from File Explorer.
Switch From address	—	Alt+S, F	Only appears after clicking '…' next to To field in OWA.
Check spelling	F7	Alt+R, S	Runs before send in Outlook 365. Disabled by default in Outlook 2016 unless turned on in File > Options > Mail > Spelling.
Forward selected message	Ctrl+F	Alt+H, F	Works even if you’re viewing a shared mailbox folder.
Save draft without sending	Ctrl+S	Alt+F, A	Drafts save automatically every 30 sec — but Ctrl+S forces immediate save.