Migrating to MSOffice 365

Hello, I’m new to this forum and new to being the IT administrator for my company (moved from a large multi-national to a small startup where I’m now in charge of IT - which isn’t my proper job!)

We currently host our domain through Dreamhost and use Gmail and Google docs for office functionality.

We would like to move to Office 365 Small Business in the near future but I have one issue that I would like to get some clarity on. We currently have about 15 office based employees and about another 15 sales reps that are scattered across the globe. These sales reps solely need a mailbox, there’s no requirement for Excel, SkyDrive etc… Given that the Office 365 Small Business has a user limit of 25 and the Midsize is quite a bit more expensive, I’d like to run 2 email servers (1 on Office 365 and the 2nd on Dreamhost or somewhere similar). I believe this is possible by setting up all users email accounts on the Dreamhost server, editing the MX records and then forwarding the 365 users to the Microsoft exchange (Office Forum).

My questions are:

  1. Is this possible with Dreamhost?
  2. Can I set up the emails on Dreamhost, if so how much do they cost?
  3. If I can, can they access their Dreamhost mailbox via iPhones etc?
  4. Will the users on MSOffice 365 be aware that there email is being forwarded (i.e. no headers, no changing of email addresses etc…)?

Many thanks in advance for you help


1) Is this possible with Dreamhost? – splitting email functions between 2 servers on the same domain won’t work the way you think. Perhaps it should on paper, but it won’t in practice, you will spend too much of your time figuring out issues, delays etc, and when you need help from one side of the other…a lot of finger pointing.
2) Can I set up the emails on Dreamhost, if so how much do they cost? Assuming you have some form of hosting with dreamhost (shared, VPS or dedicated) you can create an unlimited number dreamhost email accounts.
3) If I can, can they access their Dreamhost mailbox via iPhones etc? yes you can access dreamhost email on any device.
4) Will the users on MSOffice 365 be aware that there email is being forwarded (i.e. no headers, no changing of email addresses etc…)? Your MX record will have to point to dreamhost, at dreamhost you will have to create an email that forwards to user@yourdomain.onmicrosoft.com (you won’t be able to forward to your own domain becuase those mx records will point to dreamhost). It may in fact show up in headers and it probably will be subject to delays at times.

As a side note you will also have to “trick” the domain setup tab on office365. First setting the MX records to point to microsoft, and let the setup wizard detect that you have properly configured your domain. Then you will need to restore the MX records to point to dreamhost. Your domain management tab on the microsoft side will then forever show an error that it says needs fixing, but must be ignored to make things work in your hybrid setup.

In short, Yes I would definitely farm out your email services to office365. Comparing the service to dreamhosts email is like comparing Willie Robertson’s house to a single wide (if you haven’t seen Duck Dynasty sorry for the reference but it’s like comparing a Kia Rio with a Land Rover).

I moved a few domains and users over to office365 email and it just works. I don’t worry about mail not sending or arriving (a constant worry with dreamhost due to the frequency dreamhost IP’s show up on RBL’s).

On a final note, regarding Microsoft licensing and prices. If it’s not obvious to you which way to most economically combine the options to get enough “seats” for your organization then by all means open a ticket with microsoft support and ask for help. I opened a ticket during setup for an issue, in under hour a technician called me, understood the problem almost immediately and showed me a way to resolve it. She also volunteered that I should add a particular free add-on license. Also note that you can’t see until you actually have an account that not all of the users you create have to have the same license. So you can get say XX licensees one way as part of a large multiseat package then get others say individually or as part of another multi seat lisc.

Hi Lakerat

Thank you very much for your response. One of the things I’m trying to avoid is slowing doing the email receiving/sending process, with Gmail my colleagues rave about the fact that the email is there instantly (and on the iPhones etc…) so I don’t want to have to constantly be beaten up for delays in emails!!

I’ll take you idea of phoning them and seeing what they can do. I thought my idea was good but i had a feeling that it seemed too simple and there must be a catch somewhere along the line!!

Thanks again for you reply

PS I had no idea what Duck Dynasty was but do now as I’ve just googled it…must have missed that one on UK TV! Still not sure about his house though!

Leave Dreamhost email out of the picture then. just being honest.

My advice would be to signup for one of the 4.00/month personal accounts and register a test domain. That’s relatively inexpensive to get an account set up. The first user created by default is an admin user. If you use the $4.00 personal account (the least expensive test drive) this user won’t actually have the full admin UI. Create another user within the account and give it admin access and that user will have the full exchange admin UI (note: you won’t need to buy another lisc for this extra admin user.) This is a month to month lisc and you can drop it at anytime.) You can add your companies real domain to this same account later on and add and drop licenses to meet your needs.

Another thing, with office365 don’t count email addresses or even boxes when figuring license needs, count only actual users. for example you can have sales@yourdomain.com configured as an aliases that delivers to serveral users email addresses, sales@ is not a user and does not need a license. Additionally you could create an actual email box for CustServ@yourdomain.com and have it shared access by any number of users… while each user does need their own lisc, the additional shared email box CustServ@ does not.

Logged in as your second admin user visit the licensing tab to learn more about ALL the options that are available. There are actually A LOT more options than you can find studying microsoft.com or office365.com. Keep in mind you can mix and match on the same account as well, you just need to assign some type of lisc to each user that needs to physically log in.

I’ll leave you with that. D.D. is for some reason insanely popular in the US at the moment. It defies most logic, why would I watch that? yet my DVR is set… =]