As partially explained here, I used to have a mailbox “MyUser@MyDomain” in a MX Plan of OVH to store all my emails and an email address “MyAddress@MyDomain” which was a redirection to a gmail mailbox “MyUser@gmail.com” (People are sending me emails only on “MyAddress@MyDomain”).

All emails passed to “MyUser@gmail.com” are filtered (antispam), forwarded into my mailbox “MyUser@MyDomain” and archived at gmail (so a “backup” is kept there).

My Outlook used to be configured with IMAP to fetch emails from “MyUser@MyDomain” and SMTP to sent emails “From: MyAddress@MyDomain”

Unfortunately, mailboxes of MX Plan at OVH are limited to 5GB. So, I decided to migrate my mailbox “MyUser@MyDomain” to a “Mail Pro” account at OVH.

First, while doing so, very important, I had to define the domain as “non-authoritative”  in the “Mail Pro” account !!! Otherwise, the “Redirections” defined in the MX Plan won’t work anymore.

Next, I configured my new Mail Pro account in Outlook (NB.: this account, migrated from the MX Plan, still has the same name: “MyUser@MyDomain”). Unfortunately, once this Mail Pro account configured in Outlook, I couldn’t sent email “From: MyAddress@MyDomain” anymore. The reason is that “Mail Pro” does not know “MyAddress@MyDomain” which is defined in the MX Plan. Sending emails via the account “MyUser@MyDomain” but “From: MyAddress@MyDomain” is therefore considered as Spoofing by Mail Pro (NB.: it’s not the case within a MX Plan).

If you don’t care about the gmail antispam filtering anymore, then you can simply:

• Delete the Redirection “MyAddress@MyDomain” from the MX Plan.
• Wait for 30 sec, to be sure the delete is executed.
• Create an Alias “MyAddress@MyDomain” in your Mail Pro (it will fail if the delete is not yet executed. If this occurs, retry)

To, instead, keep the mechanism above in place:

• Create a new mailbox in the MX Plan, with simply 50MB, going to be used only to send emails via SMTP: “MyMail@MyDomain”
• Configure Outlook:
  • To use “MyAddress@MyDomain” as “From”
  • IMAP with the account of Mail Pro (“MyUser@MyDomain”)
  • SMTP with the account of MX Plan (“MyMail@MyDomain”)

It results into this schema:

Disclaimer: an SME from the community OVH reports that not only OVH is sometimes blocking outgoing emails without notifications (as those are considered as Spams, but also Gmail is rejecting many incoming emails with unclear explanation for most standard users. As a consequence, some/many (?) emails could be “silently lost” with the mechanism above….

The reason for me to use an alias is that this alias is forwarded to a “gmail” mailbox, where the antispam is quite efficient. And gmail transfers the remaining emails to my actual mailbox (on my own server/within my own domain).

I access next my actual mailbox via IMAP with Outlook. I never use the intermediary mailbox on gmail.

With the latest version of Outlook 2016, I couldn’t configure a different mail address than the “user account” of my actual mailbox (which is the mail address that I want to keep secret ).

 

I.e.: if I type Me @ BeatificaBytes.be in the config screen above, outlook will use that both for the “From” Field and as user account to connect onto my IMAP server.

This is an issue as the alias Me @ BeatificaBytes.be is not valid as an account to connect on my actual mailbox.

Obviously, I could configure Outlook with my actual account and define next my alias as a Reply Address. But than, the recipient would see my actual mail address.

The easiest is to use to good old “Mail” tool:

1. Open it via the Windows Control Panel > User Account > Mail (Microsoft Outlook 2016).
2. There, click the “Email Accounts…”
3. In the tab “Email”, click “New”…
4. And here we go!

As usually:

1. Select the option “Manual setup or …” and click “Next”
2. Select “Pop or IMAP” and click “Next”
3. Type your name and your alias email address in the user information part
4. Use your actual email address as user name in the logon information part (this is the ‘option’ never proposed by the new configuration wizard of Outlook 2016)

Et voilà…

I have been doing that for month, with Outlook 2010, on this PC and never got such an error. Fortunately I immediately thought to check the “Security” on the file. That was the issue.

That’s easy to fix:

1. Right click the attachments saved as files and select “Properties”.
2. Click Unblock.

If you have several files to be unblocked, you can also use one of the SysInternals: Streams v1.56 to unblock them all at once:

1. Open a command prompt as Administrator.
2. Run the command streams on the files to be unblocked. E.g.: streams -d *.*

Actually, a attachment saved from Outlook seems to be (?now?) considered as a file downloaded from Internet. And there are information stored in an alternate filestream that are used by Windows to block the files downloaded from Internet. The “streams” command is nuking that alternate stream. So, Windows stops blocking the files.

• First, I did enable the imap support on my gmail account and took note of all the gmail “imap parameters” for the next steps.
• Next, I did configure an imap account to access my gmail mailbox in MS Outlook (on all my PC/Laptops).
• A also configured my Google account on my Android smartphone to access my gmail mailbox , my Google Calendar and my Google Contacts.
• Finally, I did install two freeware on all my Windows PC to sync my Google Calendar and my Google Contacts with Outlook:
  • “Go Contact Sync Mod” to sync my Outlook’s Contacts with gmail (both way)
  • “Google Calendar Sync” to sync my Outlook’s Calendar with gmail (both way on my private PC, one way at work => to get my professional appointments on my personal computers but no the opposite).

Et voilà