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Exchange Cloud Setup

When I check the security setting in Outlook for my exchange cloud, it uncheck "Encryption". If I check on it, Outlook cannot connect.

Does it mean the connection betwen Outlook and Exchange Cloud doesn not encrypted ?

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AXISHK

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I'm using Exchange Online Plan 1.

Check your link, it mentions "All Office 365 for business plans includes: Security : "Cutting-edge security practices with five layers of security and proactive monitoring help keep customer data safe." I only need a secure connection between Exchange and Outlook connection. ie. Outlook client connects to Exchange Cloud.

Do I miss anything need to configure on the Portal ?

Thx
It is not related to the configuration of your Portal as it is all about money.

Have a look of Note 3 in the link above and it says:-

"Azure RMS is not included, but can be purchased as a separate add-on service or added for free to the Office 365 Education plan."

Office 365 E1 plan does not come with Azure RMS and you need to pay for that add-on service.
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I don't need Azure RMS. only to ensure Outlook is secured connected to Exchange. I review the setting for my premise Exchange where the setting should be encrypted with "Negotiate Authentication" under Logon network security....

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5 Layers of Security. Data is secured in 5 different layers - data, application, host, network, and physical and not include endpoint encryption.
Security-in-Office-365-Whitepaper.docx
I don't need Azure RMS. only to ensure Outlook is secured connected to Exchange. I review the setting for my premise Exchange where the setting should be encrypted with "Negotiate Authentication" under Logon network security....

Office 365 Message Encryption is included with Microsoft Azure Rights Management (Azure RMS). You can sign-up for a 30-day trial of the service from the Office 365 Rights Management trial portal here: Azure Rights Management plan. In order to use Office 365 Message Encryption, you must meet the following criteria:
1. If using Office 365, you need to have a plan that includes Azure RMS or can support Azure RMS purchased separately. To learn which plans include Azure RMS, see Office 365 Plan Options.
2. If using on-premises mailboxes, you must route email through Exchange Online, either by using Exchange Online Protection for email filtering or by establishing hybrid mail flow.

Source: https://technet.microsoft.com/en-us/library/dn569285.aspx

You need Office 365 Message Encryption if you want endpoint encryption.
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So, currently outlook is not securely connected to Exchange server and all the content is sent as plain text ?

Under my current plan, I need to through web access ssl (https) to ensure secure connection, correct ?

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