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Hi Everyone,

I work for a company who use Outlook 2016 and Office 365 for email, let us call them ParentCompany1 [parentcompany1.com]. Last year, ParentCompany 1 acquired a new company, let us call them NewCompany2 [newcompany2.com]. NewCompany 2 uses Kerio, currently running Release 9.2.0, using Outlook in conjunction with the Kerio Offline Connector.

Following the acquisition, ParentCompany1 created new Office 365 accounts for the users in NewCompany 2, giving each of them a parentcompany1.com email address and creating a forwarding rule to automatically forward all email to their respective newcompany2.com email addresses.

Users in NewCompany2, installed Office, including Outlook 2016 from their new Office 365 account, setting up their parentcompany1.com email. They then added their old newcompany2.com accounts using the Kerio Offline Connector.

Since then, the NewCompany2 users cannot send emails from their respective newcompany2.com mailbox to a parentcompany1.com recipient when adding any external recipient to the same message. For example, I am joe.bloggs@newcompany2.com and I create and email to john.bloggs@gmail.com (external) and copy my colleague in the ParentCompany1 tom.manager@parentcompany1.com, the message will deliver to john.bloggs@gmail.com (external) but not to tom.manager<_at_>parentcompany1.com.

All other combinations work fine.

Has anyone experienced this scenario before or know of any solution to the issue?

Ideally, we would like both accounts to co-exits, without having to switch profiles. I've been told from my colleagues, who use Kerio, that this was possible with Outlook 2013.

Any help would be GREATLY appreciated.

Bud Durland

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From what I've read, getting a single OutLook profile to connect to both Exchange and Kerio Connect, while technically possible, is a bumpy road. No doubt the users in NewCompany2 are using the Kerio Offline Connector (KOFF) If I had to do it, it would be something like this:

  1. Export Calendar and personal contacts from the Kerio account to a .PST file
  2. Make a new Outlook profile, connect to Exchange. Use the Exchange server to send all e-mail
  3. Import the calendar and contacts from the file created in step 1
  4. Configure an IMAP account in Outlook to connect to the Kerio Connect server, to read old e-mails
  5. Create an alternate send identity in OutLook for the times when your e-mail has to look like it came from 'NewCompany2'

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