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How to connect to Office 365 email


Since upgrading to office 365 I have been unable to connect using the various ‘use microsoft outlook’ to rad and send emails. How do I configure to send and receive with outlook? Any ideas? It sounds as though Office 365 is not supported ATM.

I do have outlook installed on the local computer which connects fine but the option to select is still grayed out.



Hey Nigel,

You are correct that Outlook through Office 365 is not supported at this time. There are ways to work around this limitation.

Email Input

First of all, instead of using Outlook you can still capture emails using POP3.

If that’s not an option for you, then it’s possible to configure Outlook to drop files in folders when certain emailing conditions are met. You’d then configure your processes to have “Folder Capture” inputs instead of “Email Input” inputs. We have an internal guide prepared on this, if you’re interested.

Email Output

The plugin that produces email output through Connect is called the “Create Email Content” plugin. The “Send Email” plugin is a legacy plugin that is included in Connect’s Workflow because Connect’s Workflow it is designed to be backwards-compatible when upgrading from Suite to Connect.

The Create Email Content plugin sends emails over SMTP, and it supports TLS encryption. If what you’re looking for out of sending through Outlook is to verify sent items, what you could do instead is have the sender also be a bcc recipient. So instead of checking the sent items, those emails would appear in the inbox. The bcc recipient of course doesn’t have to be the sender and you can easily set up rules in Outlook to filter those emails into a specific folder, instead of cluttering the main inbox.

The Send Email plugin supports SMTP emailing, but does not support TLS encryption.

If you want to send an email without going through the Connect plugins, and your email server requires TLS encryption, then your last option would be to send the email through a script using the “Run Script” task. We have script examples that we could provide, if you’re interested.

Hi Stephen

Many thanks for your reply it was very helpful. I do us Sparkpost for sending emails which works well and I do use both the send email options. The main problem is the incoming where Office 365 pop3 settings don’t work due to he security so I was needing to do that locally. It is a shame that the option to just select use Microsoft outlook does not appear to work anymore as that worked well. The guide and examples you have would be very useful to help me sort this.

Thanks again


I’m going to be looking into getting the “Capture emails from any Outlook version” guide made publicly available, but for the meantime if you provide me with your email address I can send it to you personally.

Hi how do I give you my email privately?


There won’t be any need for that. The guide has now been made publicly available:


Hi Stephen

That works well thanks.




I have set up the outlook folders as suggested and it works well - the workflow picks up the file and creates the metadata required. As I mentioned before I manage to be able to send emails using the legacy ‘Send Emails’ plug in but I am having problems using the Create Email Content plugin. When I try in the design the email sends OK but in workflow I keep getting the error - unconfigured sending domain <example.com> and I don’t know where this domain is set. In the designer the files send fine and are configured via the WIndows|Preferences|General tab but I cannot get this to work for workflow.

When I test the configuration by clicking Test SMTP settings on the Email Info tab of the Create Email Content plug in I get 5.7.1 Unconfigured Sending Domain <example.com>.When I run the workflow then the the message I get back from Sparkpost is:-






550 5.7.1 Unconfigured Sending Domain <example.com>

DO you know where these setting are set please?

The Preferences are set for the preferences|Behaviour|OLConnect and also in the Email Info tab of the plug in and you can set the from address but not the sending domain. Any ideas on this? This also applies when trying to get the OLsend example to work.



Hi Nigel,

The from address goes in the “Sender Address” field, and the sending domain goes in the “Mail host” field.


Hi Stephen

Thanks for you ongoing help with this one - I should have said that I have set the sender address field correctly and the other settings in the plug in. I should have attached a screen shot - which I have done now. I should also mention that this is a test and development licence - I don’t know of that makes any difference. Also attached is the feedback from spark post that shows the sender address. I really don’t understand where the sender address is coming from.

Any help much appreciated



Hi Nigel,

It looks like you’ve entered valid information, I’m not sure what the issue could be.

You may want to open a support ticket so we can assist you further with this.

Switched comment modes… carry on… nothing to see here…


One other thing you may consider is using a proxy between PlanetPress and Office365. I’ve seen STunnel successfully used for this. STunnel could potentially run on the same server as PlanetPress providing the secure “tunnel” to O365 servers that PlanetPress needs for email capture (POP3) and email send (SMTP). The process is transparent to PlanetPress as it thinks it’s dealing with a local server. This would avoid having to use Outlook all together (if that’s important).

Here are some configurations that should work for STunnel. (Adapted from here)

[POP3 Incoming]
client = yes
accept = 110
connect = outlook.office365.com:995
verifyChain = yes
CAfile = ca-certs.pem
checkHost = outlook.office365.com

[SMTP Outgoing]
client = yes
protocol = smtp
accept = 25
connect = smtp.office365.com:587
CAfile = ca-certs.pem
verifyChain = yes
checkHost = smtp.office365.com