With irritating regularity, Outlook will not actually sync my local inbox - even after the 'Synchronize Now' button is used multiple times.

In these scenarios, I can attempt to quit and restart outlook (I frequently need to force quit), but the inbox still won't actually sync. If I want to actually receive new messages, I need to fully reboot my machine for outlook to pick up new messages. Force-syncing doesn't resolve the issue, quitting / force-quitting and re-starting Outlook doesn't solve the issue, only rebooting the machine does.

I am running on an up-to-date version of Mojave, and I keep the Outlook app updated regularly. This issue has persisted for a while now

Feature: Vault Folder

I want a "vault" folder with hardened encryption, access and authentication.

Imagine similar features to [OneDrive's Personal Vault](https://www.microsoft.com/en-us/microsoft-365/blog/2019/06/25/onedrive-personal-vault-added-security-onedrive-additional-storage/). Essentially I want similar features in Outlook.

Core Business Requirements

The core concepts of this suggested folder feature:

• Hardened encryption at rest


• Effective privacy enhancements


• Lockable, auto-lock and timeout


• Additional authentication
  


• Secure multi-factor authentication options

Nice to See

I would rather see some Vault-like feature than none.
To see this implemented "right" in my own view would need

• Recovery Key Management


• Strong Open Cryptography


• Strong MFA


• Inhibited Access


• Exfiltration Protection


• Access Restrictions


• Privacy by Default


• Secure Development


• Audited / Certified

Most of that is standard security advice. I've made some expounding suggestions below that help convey some particular visions I had.

Strong MFA

"Strong MFA" is begging you not to SMS or Email codes as sole 2FA alone.
- No SMS - if you have my phone you have my mailbox as well as SMS, keep my vault locked
- No Email - if you are in my mailbox, you can get my email, keep my vault locked
- Hardware 2FA - U2F is what all the cool kids want, I wouldn't blame you for other hw keys
- Device HW Trust - use device hardware security, don't unlock on devices without hw trust
- Biometric Factors - only as quick unlocking once stronger factors are confirmed

Inhibited Access

It should go without saying that only the mailbox owner should access the content. For security I'd tolerate a lot more restriction with this content. I expect a Vault would need to be inaccessible in the ways that other mailbox content is not:
- no delegate access
- no web / OWA access
- no plugin access
- no o365 integrations
- no OS integrations
- no third-party integrations
- geographic location limits
- time-delayed recovery
- no admin nor other user access

Privacy by Default

The balance of privacy and data-driven features makes sense for Outlook. However, I envision a Vault as a safe-haven where I can opt my content into additional privacy with sensible privacy deafaults:
- no telemetry
- no addresses added to contacts
- no unencrypted logging
- no unencrypted index
- no reminders
- no notification details
- no search while locked

Exfiltration Protection

I envision moving items into and out of the Vault folder as the only way to access them. It should be hardened, but I'd expect reduced actions on all items in a Vault for exfiltration safety:
- no forwarding
- no delete while locked
- no sending
- no rules processing
- no macros
- no export
- no printing
- no API access
- no admin ownership access
- no archiving
- no meeting creation
- no permission exceptions

Give the ability to designate a default sender address not just a default reply-from addr. I have both personal and work e-mail on my office computer which is acceptable use in my company. However, Outlook chooses the sender depending on what message I have currently selected. There is no way to specify that mail should always be sent from my work address. This has resulted in me accidently sending potentially sensitive company information through my Google mail. In addition to the potential security problem this represents, having the wrong sender confuses people from my company. Please help me stop getting in trouble with my boss.

Prior to migrating to O365, we were using Zoho Email and I have had few email alias for various purposes like an alias for subscription, some I had used earlier (longer ones) before I created a shorter version of the email (for easy usage).

Also, helps be identify which ones I had subscribed and which ones I had not - so, I can easily filter out the ones I had not originally subscribed to. With the current implemention of redirecting emails from all alias to the default alias, I'm unable to identify the same. I'm also hoping this redirection doesn't mark the email as "read" for the email trackers.

In the past, when a client would sent me an email to one of the earlier alias, I was able to respond back using the same alias as from address - which helped continue the trust and not cause any confusion. And I was all the time able to see to which alias the email was sent to/was received.

Other times, I'm at times required to respond to support teams from the email (alias) that I had originally registered with them - so, I'll need to switch to either switch default alias or change the email that i was using in the app. In most cases it works fine, as the name is still the same, just the email has got shorter to only the first name, for example. Not too concerned here, but more on the earlier points.

Atleast a way to find out which was the alias the email was first sent to, would be great to start with...