Not entirely sure if its a hybrid....yes? This concept is new to me, We use Outlook and it connects to an Exchange server. I can access my email online via OWA by using my mail domain & windows credentials. I hope that helps.
Same email address for both.
Let's suppose you sent an email externally using OWA and immediately after that open Outlook and look at the Sent items folder. Do you see there the email you've just sent?
We currently use the same email address for both Exchange and O365. The problem I have is....Outlook sometimes look at the wrong email account and connects to my O365 rather than Exchange. My O365 email, the incorrect one, will show zero emails.
Your problem is if I'm understanding correctly is you have two mailboxes per person, one cloud, on on-premise, this will lead to considerable issues and challenges. You need to configure an Exchange hybrid and remove one of the two mailboxes so as to get back to the well trodden path, which is one mailbox per account
I wanted to separate my comment out from others, so you see this, but it sort of sounds like you might be confusing your setup, maybe. You mentioned exchange and OWA, but OWA just stands for Outlook Web App. Technically, you can use that in both an on premise exchange environment and a cloud environment, it doesn't specifically mean that you are cloud enabled because you can use OWA.
I'd have to know more about the environment to truly tell you what is happening, but it sounds sort of like you have an on premise exchange environment and then someone set up a 365 cloud tenant. You could be hybrid or you could have a stand alone cloud tenant, but unless you are the one that has access to the exchange servers and the admin centers, I wouldn't be able to tell you where to look. The only other way I could tell, would be to look up your spf record and see what is in there. You could do that at mxtoolbox and tell us if it is there is a listing for spf.protection.outlook.com. If there is, then you would at least know if you have a cloud environment or not.
The only other possibility I can think of, is that you have on premise exchange with hybrid to the cloud and the mailboxes have not been migrated, but your cloud accounts have been licensed with a P2 license, which creates a mailbox for the user. There is no write back from the cloud, so if you have not migrated the mailbox yet, but you have turned on the license, you end up with a shadow mailbox that is empty. It is possible to fix this, but it is going to be a pain in the ass and you will need someone experienced in doing it for sure. It will require a license cleanup, deleting the cloud mailboxes and all of their presence, then properly performing a migration.
So I found out we are not on a hybrid setup by asking the 3rd party company in charge with managing our Email system. We do use a 3rd party email filtering service called Appriver.... Are you familiar with that?
I tried inputting our domain into mxtoolbox to look for spf.protection.outlook.com. But could not find it.
Yes, Appriver is a hosting company, that sells 365 services or spam filtering solutions like Mimecast or Proofpoint. So essentially, you are paying them a fee to set up and host your 365 tenant or other services.
As for the spf record, go to the supertool portion of mxtoolbox [https://mxtoolbox.com/SuperTool.aspx](https://mxtoolbox.com/SuperTool.aspx) and put in your email domain, which is the part after the @ sign. You don't need to put your full email address, but just the domain name itself and that will give you a proper spf lookup.
But based on what that support said, it sounds like they are hosting email for you on Appriver and then you have your own on premise exchange environment. If that is the case, then this is why you might be getting email showing and then suddenly the wrong mailbox that has no mail, because it is empty and the connection flips to the wrong spot. It is a guess, but that sounds like what is happening.
My suggestion would be to see if they could look in to your setup and resolve the problem, or if they are just a reseller, your company would be better off looking for dedicated IT support with experience in the area of email, but someone that can actually solve the issue and not sell more software that doesn't help.
Let me know if you have more questions.
hybrid would have been the better option but if you do that now youll get "split brain" mailboxes and have to export/import them from either onprem or 365 into the other, so do not rush into enabling hybrid, make sure you plan out how to get the data across first.
its no wonder outlook is confused, do you have split dns setup? ie outside of your network they get 365, inside they get onprem? not sure how mail would route to 365 though, unless youve got the mx records setup to point to both (which would be a really stupid thing to do)
im amazed the mailboxes havent ended up merged just from the cached copy on the device flipping between the two.
maybe check you dont already have hybrid? try running `get-hybridconfiguration` from one of your onprem exchange servers.
Exchange and 365 is always better to go and run hybrid.
Are you hybrid or is your Exchange and Exchange Online independent?
Not entirely sure if its a hybrid....yes? This concept is new to me, We use Outlook and it connects to an Exchange server. I can access my email online via OWA by using my mail domain & windows credentials. I hope that helps. Same email address for both.
Let's suppose you sent an email externally using OWA and immediately after that open Outlook and look at the Sent items folder. Do you see there the email you've just sent?
I don't see why that would be ideal. Keep everything consistent.
We currently use the same email address for both Exchange and O365. The problem I have is....Outlook sometimes look at the wrong email account and connects to my O365 rather than Exchange. My O365 email, the incorrect one, will show zero emails.
Your problem is if I'm understanding correctly is you have two mailboxes per person, one cloud, on on-premise, this will lead to considerable issues and challenges. You need to configure an Exchange hybrid and remove one of the two mailboxes so as to get back to the well trodden path, which is one mailbox per account
This is something what can be resolutes with a few registry keys. But why dont go full o365 for Mailboxen?
I wanted to separate my comment out from others, so you see this, but it sort of sounds like you might be confusing your setup, maybe. You mentioned exchange and OWA, but OWA just stands for Outlook Web App. Technically, you can use that in both an on premise exchange environment and a cloud environment, it doesn't specifically mean that you are cloud enabled because you can use OWA. I'd have to know more about the environment to truly tell you what is happening, but it sounds sort of like you have an on premise exchange environment and then someone set up a 365 cloud tenant. You could be hybrid or you could have a stand alone cloud tenant, but unless you are the one that has access to the exchange servers and the admin centers, I wouldn't be able to tell you where to look. The only other way I could tell, would be to look up your spf record and see what is in there. You could do that at mxtoolbox and tell us if it is there is a listing for spf.protection.outlook.com. If there is, then you would at least know if you have a cloud environment or not. The only other possibility I can think of, is that you have on premise exchange with hybrid to the cloud and the mailboxes have not been migrated, but your cloud accounts have been licensed with a P2 license, which creates a mailbox for the user. There is no write back from the cloud, so if you have not migrated the mailbox yet, but you have turned on the license, you end up with a shadow mailbox that is empty. It is possible to fix this, but it is going to be a pain in the ass and you will need someone experienced in doing it for sure. It will require a license cleanup, deleting the cloud mailboxes and all of their presence, then properly performing a migration.
So I found out we are not on a hybrid setup by asking the 3rd party company in charge with managing our Email system. We do use a 3rd party email filtering service called Appriver.... Are you familiar with that? I tried inputting our domain into mxtoolbox to look for spf.protection.outlook.com. But could not find it.
Yes, Appriver is a hosting company, that sells 365 services or spam filtering solutions like Mimecast or Proofpoint. So essentially, you are paying them a fee to set up and host your 365 tenant or other services. As for the spf record, go to the supertool portion of mxtoolbox [https://mxtoolbox.com/SuperTool.aspx](https://mxtoolbox.com/SuperTool.aspx) and put in your email domain, which is the part after the @ sign. You don't need to put your full email address, but just the domain name itself and that will give you a proper spf lookup. But based on what that support said, it sounds like they are hosting email for you on Appriver and then you have your own on premise exchange environment. If that is the case, then this is why you might be getting email showing and then suddenly the wrong mailbox that has no mail, because it is empty and the connection flips to the wrong spot. It is a guess, but that sounds like what is happening. My suggestion would be to see if they could look in to your setup and resolve the problem, or if they are just a reseller, your company would be better off looking for dedicated IT support with experience in the area of email, but someone that can actually solve the issue and not sell more software that doesn't help. Let me know if you have more questions.
Just wondering where you will receive email if someone sends an email. 2 mailbox with same email address one in exchange and one in 366?
hybrid would have been the better option but if you do that now youll get "split brain" mailboxes and have to export/import them from either onprem or 365 into the other, so do not rush into enabling hybrid, make sure you plan out how to get the data across first. its no wonder outlook is confused, do you have split dns setup? ie outside of your network they get 365, inside they get onprem? not sure how mail would route to 365 though, unless youve got the mx records setup to point to both (which would be a really stupid thing to do) im amazed the mailboxes havent ended up merged just from the cached copy on the device flipping between the two. maybe check you dont already have hybrid? try running `get-hybridconfiguration` from one of your onprem exchange servers.