Cisco Cloud Security Interoperability with Microsoft Office 365

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1 White Paper Cisco Cloud Security Interoperability with Microsoft Office 365 We ve all been witness to the cloud evolution and the technologies that have been driven by moving operations and resources off-site to provide services that were traditionally housed internally. The migration to online services has provided many benefits to companies; small businesses can now have enterprise class redundancy and disaster recovery without the capital outlay for telecommunication, network and server resources. Scalability, reliability and numerous other factors have led to this evolution. Companies looking to gain competitive advantages and realizing that , once thought to be not mission critical like financials, has become business critical. Companies conduct a large portion of their business today via . Banking, trading, sales contracts, legal documents all are transferred securely and non-securely via electronic mail. Companies have realized that a logical step to moving to the cloud is by moving mailboxes to hosted providers. Microsoft Office 365 Hosted Mailboxes Microsoft Exchange has become the standard system used by many mid to large-scale organizations. In order to gain an even larger market share Microsoft has introduced Office365.com, which will allow even a sole proprietorship company to reap the benefits of Exchange without having to have the technical staff or the hardware necessary for an Active Directory and Exchange infrastructure. Office365 is much more than just and calendaring, it encompasses other Microsoft applications delivered via the public Internet. For the purpose of this paper we will stay focused on and mailboxes provided by Office365. Microsoft Exchange Online Protection (EOP) Microsoft EOP is a hosted filtering service that provides protection for Office365. FOPE provides the following list of features: Antispam Antivirus Policy enforcement Disaster Recovery Directory services SLA s provided by Microsoft EOP are as follows: Spam Effectiveness >99% False Positives <1:250,000 Virus detection and blocking of 100% of known viruses Monthly uptime of % Messages queuing for 2 days when the on-premises server cannot accept mail More information available at Cisco and/or its affiliates. All rights reserved. This document is Cisco Public. Page 1 of 6

2 While these SLA s and Microsoft market position in Exchange would point customers towards using Office 365 with EOP as their security solution, customer adoption to a more in-depth security solution has led to Microsoft having to provide mechanisms to interoperate with 3rd party systems like DLP (Data Loss Prevention) or industry leading Security vendors like Cisco Systems, Inc. s, Security Appliance, cloud and on premise solutions Cisco Security Services Based on the same industry-leading technology that protects 50 percent of Fortune 1000 companies from inbound and outbound threats, the Cisco Cloud Security service allows customers to reduce their on-site data center footprint and out task the management of their security to trusted security experts. It provides a dedicated security infrastructure in multiple, resilient Cisco data centers to enable the highest levels of service availability and data protection. Customers retain access to (and visibility of) the hosted infrastructure. With comprehensive reporting and message tracking, maximum administrative flexibility is assured. This unique service is all-inclusive with software, hardware and support bundled together for simplicity. Best-in-Class Features: Powered by Cisco Talos, the industry s largest threat intelligence service Industry leading Anti-SPAM Award winning Anti-Virus from Sophos and McAfee Targeted Attack Prevention with Cisco AMP Advanced Malware Protection RSA Data Loss Prevention Integrated Message Level Encryption S/MIME encryption Web in protection with URL categorization and reputation Content Filtering Inbound / Outbound Transport Layer Security (TLS) Anti-phishing and day-0 protection with Outbreak Filters Role Based Administration % uptime False positive rate of less than 1 in 1,000,000 Co-management Multiple US and European Datacenters for redundancy Dedicated IP addresses to avoid shared fate blacklisting Financially backed Service Level Agreement Cisco is proud to be recognized as a leader in the Gartner Magic Quadrant for Gateways 2014 Cisco Talos Cisco Security is part of Cisco s comprehensive family of network security products and services. Organizations are better positioned to detect and respond to threats when using best-of-breed products and services that fall under one vendor umbrella for example, because Cisco Security can talk to Cisco Adaptive Security Appliances, both can be managed under the same security policy and threats can be identified and addressed faster. Cisco Security leverages Cisco Talos, which sees 35 percent of the world s traffic, 75 TB of web data per day, 13 billion web requests, 1.6 million deployed devices, and more than 150 million endpoints. Cisco products integrate technology from solutions like Cisco Web Security and Cisco Sourcefire, which addresses unwanted and potentially 2015 Cisco and/or its affiliates. All rights reserved. This document is Cisco Public. Page 2 of 6

3 malicious URLs and file attachments in . Organizations need this multi-vector intelligence in order to have best-inclass security and protect themselves from the latest of blended threats. Why do you need Cisco Cloud Security with Office 365? In addition to the best-in-class messaging security features listed above, the prime reasons why you will benefit from Cisco Cloud Security are: Industry leading protection from based threats, including phishing and targeted attacks, with the highest efficacy (99% catch rate, < 1/1M false positives) Top controls for Data Loss Prevention (DLP) and Secure Messaging, essential for a protected and secure organization Integrated message level encryption no 3rd party products necessary Ability to leverage Cisco Talos, for protection against multi-vector sophisticated attacks Near real time graphical message tracking real time available from command line interface With a dedicated client infrastructure, organizations will benefit by having no shared fate and reduced risk of outages caused by another customer Dedicated monitoring and support for Cisco Hosted Security customers Customer controlled reporting with Cisco support available to assist if needed Integrating Office 365 with Cisco Cloud Security Fortunately for Office 365 customers Microsoft has made integration with 3rd party systems fairly easy. The ability inside of the Office365 environment to create Smart Host connectors for EOP to route to these systems is well documented. See Microsoft Exchange library. Routing Inbound mail for SPAM filtering to Cisco Cloud Security routing takes place via the use of Mail Exchange (MX) records. These records are DNS entries that tell systems where to deliver . In a non-hosted environment this record typically points to the customers on-premise MTA (message transfer agent), which could be a Microsoft Exchange server, or any X flavored Sendmail variant. The MX records points to the IP address (usually an inbound NAT on the firewall), which accepts incoming SMTP connections. This MTA may also be a special purpose appliance like the Cisco Security Appliance (ESA). As seen in the below diagram customers may have many MX records pointing to various IP addresses for redundancy. Cisco Hosted Security Services provides customers with 2 MX records to provide MX redundancy in addition to datacenter redundancy Cisco and/or its affiliates. All rights reserved. This document is Cisco Public. Page 3 of 6

4 Let examine how the customer Acme, Inc. (a fictitious company), would migrate their security to Microsoft Office365 and Cisco Cloud Security. Today Acme, Inc. houses their systems internally and all messages are filtered by a homegrown application that hasn t provided the level of protection necessary for Acme s employees. Acme has made the decision to move both the mailboxes for the employees as well as the security infrastructure to the cloud and has selected a combination of Microsoft Office365 and Cisco Cloud Security. Acme s IT staff has arranged for both services to be active and has configured the Office365 environment with their users mailboxes. Acme s current mx record points to mail.acme.com. The Cisco Cloud Security environment has been configured and is ready for production traffic. MX records of mx1.acme.iphmx.com and mx2.acme.iphmx.com have been created. These records point to the Cisco Security Appliances hosted in redundant Cisco s datacenters. Acme and their business partner have configured the Cisco Cloud protection to route received for Acme s domain to the Microsoft Office365 servers where they will be delivered to the end users mailbox. Acme s IT staff changes the companies DNS MX records from mail.acme.com to mx1 and mx2.acme.iphmx.com and over a period of up to 24 hours DNS server around the Internet will detect this change and begin forwarding to the Cisco Cloud Security Appliances for Acme. The messages will be scanned incoming for Anti-Spam, Anti-Virus, malicious file attachments, and malicious URL s and other hygiene will be performed prior to delivery to Office365. Routing Outbound Delivery from Office 365 to Cisco Cloud Security Acme s Executive staff has made it clear they want leaving their organization to adhere to various government regulations like HIPAA and Sarbanes Oxley. In order to accomplish this Acme s IT staff has made the decision to route outbound through the Cisco Cloud where policy enforcement using the RSA Data Loss Prevention modules as well as the integrated Cisco Encryption can be utilized. In order to route the messages from the Microsoft Office 365 mailboxes to Cisco an Outbound Connector must be configured in the FOPE system. For more information see 1. In the EOP Admin Center select Exchange then go to Mail Flow and click Connectors2. In the Connectors select Outbound Connectors and then Add 3. Name the connector: Outbound to Cisco Cloud 2015 Cisco and/or its affiliates. All rights reserved. This document is Cisco Public. Page 4 of 6

5 4. Specify the recipient domain as *.* 5. Deliver all messages to the following destination: mx1.acme.iphmx.com and mx2.acme.iphmx.com 6. Select Transport Layer Security (TLS) and select validation against self-signed certificate 7. Save your changes In the Cisco Cloud Security configure the following 1. Mail Policies/HAT Overview 2. Add the Office 365 domain: acme.onmicrosoft.com to the RELAYLIST policy and Commit changes Now Acme Inc has all the benefits of hosted mailboxes by Office 365 and the industries best protection from Cisco Cloud Security. Cloud Hosted Security with Office Cisco and/or its affiliates. All rights reserved. This document is Cisco Public. Page 5 of 6

6 Printed in USA C / Cisco and/or its affiliates. All rights reserved. This document is Cisco Public. Page 6 of 6

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