{"id":6130,"date":"2015-10-08T12:00:23","date_gmt":"2015-10-08T11:00:23","guid":{"rendered":"http:\/\/www.markwilson.co.uk\/blog\/?p=6130"},"modified":"2015-10-12T16:06:20","modified_gmt":"2015-10-12T15:06:20","slug":"office-365-and-proxy-servers-like-oil-and-water","status":"publish","type":"post","link":"https:\/\/www.markwilson.co.uk\/blog\/2015\/10\/office-365-and-proxy-servers-like-oil-and-water.htm","title":{"rendered":"Office 365 and proxy servers: like oil and water?"},"content":{"rendered":"<p>Office 365 and proxy servers don&#8217;t mix very well. Well, to be more accurate, thousands of Outlook, Skype for Business and OneDrive for Business clients, each with multiple connections to online services can quickly build up to a lot of (persistent) connections.\u00a0If you haven&#8217;t already, it&#8217;s well-worth reading <a href=\"http:\/\/blogs.technet.com\/b\/onthewire\/archive\/2014\/06\/18\/ensuring-your-proxy-server-can-scale-to-handle-office-365-traffic.aspx\">Paul Collinge&#8217;s\u00a0blog post on ensuring your proxy server can scale to\u00a0handle Office 365 traffic<\/a>.<\/p>\n<p>Microsoft recommends that the network is configured to allow unauthenticated\u00a0direct outbound access to <a href=\"https:\/\/support.office.com\/en-gb\/article\/Office-365-URLs-and-IP-address-ranges-8548a211-3fe7-47cb-abb1-355ea5aa88a2\">a published list of URLs and IP ranges<\/a>\u00a0(there&#8217;s also <a href=\"http:\/\/go.microsoft.com\/fwlink\/p\/?linkid=236301\">an RSS feed<\/a>)\u00a0&#8211; although I&#8217;ve had customers who take issue with this and don&#8217;t think it&#8217;s a reasonable expectation in the enterprise. My view? You&#8217;re adopting cloud services; your network boundary has moved (disappeared?) and the approach you take to managing the connectivity between services needs to change.<\/p>\n<p>Perhaps as more people take advantage of services like\u00a0<a href=\"https:\/\/blogs.office.com\/2015\/09\/29\/announcing-general-availability-of-expressroute-for-office-365\/\">ExpressRoute for Office 365<\/a>,\u00a0things will change but, for now, every Office 365 implementation I work on seems to involve a degree of proxy bypassing&#8230;<\/p>\n<p>Some of the issues I experienced in a recent implementation\u00a0included:<\/p>\n<ul>\n<li><em>OneDrive for business unable to perform an initial synchronisation, but fine on subsequent syncs.<\/em> It seems that the OneDrive client downloads http:\/\/clientconfig.microsoftonline-p.net\/fplist.xml when it first syncs.\u00a0We could get it to work when\u00a0going through a different proxy server, or direct to the Internet; but\u00a0the main proxy server had to have a list of trusted sites added. The managed services provider\u00a0had previously\u00a0allowed access to\u00a0some known IP addresses (a risky strategy as they change so frequently and the use of content delivery networks means they are not always under Microsoft&#8217;s control), but\u00a0the proxy server had the capability to\u00a0trust a list of target\u00a0URLs too.<\/li>\n<li><em>Outlook unable to reliably\u00a0redirect\u00a0after Exchange mailboxes were migrated to Exchange Online.<\/em> In this case, we found that, even with the trusted URLs in place on the proxy, as part of the Outlook\u00a0Autodiscover process, Outlook was trying to contact autodiscover-s.outlook.com. The proxy wasn&#8217;t allowing unauthenticated access and Outlook didn&#8217;t know how to cope with the authentication request. Once autodiscover-s.outlook.com had been added to the proxy server&#8217;s unauthenticated access list, Outlook\u00a0Autodiscover began to work as intended.<\/li>\n<li><em>Lync\/Skype for Business Online calls working internally, but not with external parties<\/em>. Users dropping off the call after a few seconds. We still haven&#8217;t got to the bottom of this, but strongly suspect the network configuration&#8230;<\/li>\n<li><em>Exchange Hybrid free\/busy information not available cross-premises<\/em>. Again, this seems to be related to the Exchange servers&#8217; ability to see the Internet (free\/busy lookups are performed by the server, not the client).<\/li>\n<\/ul>\n<h3>Further reading<\/h3>\n<ul>\n<li>How to troubleshoot non-browser apps that can\u2019t sign in to Office 365, Azure, or Intune (<a href=\"https:\/\/support.microsoft.com\/en-us\/kb\/2637629\">Microsoft knowledge base article 2637629<\/a>)<\/li>\n<li>Tony Brown&#8217;s Microsoft Messaging User Group post on <a href=\"http:\/\/www.mmug.co.uk\/blogs\/tony-brown\/10-office-365-and-proxy-servers\">Office 365 and proxy servers<\/a>.<\/li>\n<li>Jesper St\u00e5hle&#8217;s\u00a0<a href=\"http:\/\/jesperstahle.azurewebsites.net\/?p=972\">&#8220;lost\u00a0documentation&#8221; for Office 365 and web proxies<\/a>.<\/li>\n<\/ul>\n","protected":false},"excerpt":{"rendered":"<p>Office 365 and proxy servers don&#8217;t mix very well. Well, to be more accurate, thousands of Outlook, Skype for Business and OneDrive for Business clients, each with multiple connections to online services can quickly build up to a lot of (persistent) connections.\u00a0If you haven&#8217;t already, it&#8217;s well-worth reading Paul Collinge&#8217;s\u00a0blog post on ensuring your proxy &hellip; <a href=\"https:\/\/www.markwilson.co.uk\/blog\/2015\/10\/office-365-and-proxy-servers-like-oil-and-water.htm\" class=\"more-link\">Continue reading <span class=\"screen-reader-text\">Office 365 and proxy servers: like oil and water?<\/span><\/a><\/p>\n","protected":false},"author":2,"featured_media":0,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_exactmetrics_skip_tracking":false,"_exactmetrics_sitenote_active":false,"_exactmetrics_sitenote_note":"","_exactmetrics_sitenote_category":0,"_jetpack_memberships_contains_paid_content":false,"footnotes":""},"categories":[218],"tags":[217,22],"class_list":["post-6130","post","type-post","status-publish","format-standard","hentry","category-technology","tag-office-365","tag-networks"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.6 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Office 365 and proxy servers: like oil and water? 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During the process, we used a few tools (as well as examining the\u2026","rel":"","context":"In &quot;Technology&quot;","block_context":{"text":"Technology","link":"https:\/\/www.markwilson.co.uk\/blog\/topic\/technology"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":5997,"url":"https:\/\/www.markwilson.co.uk\/blog\/2015\/09\/pick-the-primary-domain-when-activating-yammer-on-an-office-365-tenant.htm","url_meta":{"origin":6130,"position":1},"title":"Pick the primary domain when activating Yammer on an Office 365 tenant","author":"Mark Wilson","date":"Wednesday 16 September 2015","format":false,"excerpt":"One of the challenges with working with Office 365 for a living is that it now offers a pretty broad range of services. I work in a unified communications and messaging team (think Skype for Business and Exchange) but I also need to know about: Windows identity topics including Active\u2026","rel":"","context":"In &quot;Technology&quot;","block_context":{"text":"Technology","link":"https:\/\/www.markwilson.co.uk\/blog\/topic\/technology"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":2590,"url":"https:\/\/www.markwilson.co.uk\/blog\/2011\/05\/changing-the-primary-email-address-for-office-365-users.htm","url_meta":{"origin":6130,"position":2},"title":"Changing the primary email address for Office 365 users","author":"Mark Wilson","date":"Monday 16 May 2011","format":false,"excerpt":"In my recent post about configuring DNS for Office 365, I mentioned that Microsoft creates mailboxes in the form of user@subdomain.onmicrosoft.com.\u00a0 I outlined the steps for adding\u00a0so-called \"vanity\" domains, after which additional (proxy) email addresses can be specified but any outbound messages will still be sent from the onmicrosoft.com address\u2026","rel":"","context":"In &quot;Technology&quot;","block_context":{"text":"Technology","link":"https:\/\/www.markwilson.co.uk\/blog\/topic\/technology"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":6091,"url":"https:\/\/www.markwilson.co.uk\/blog\/2015\/09\/office-365-dns-settings-in-a-hybrid-environment.htm","url_meta":{"origin":6130,"position":3},"title":"Office 365 DNS settings in a hybrid environment","author":"Mark Wilson","date":"Friday 25 September 2015","format":false,"excerpt":"The Office 365 Admin Center does a great job of helping administrators determine the DNS settings that are required to use a domain with Office 365; however it's far from perfect. 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Check the client firewall","author":"Mark Wilson","date":"Saturday 26 October 2013","format":false,"excerpt":"I've written previously about managing my Office 365 tenant using Windows PowerShell\u00a0(Microsoft has since provided its own documentation on the topic) but I tried today and found that I couldn't get a connection. Every time I tried to create a session, the response came back as: [ps.outlook.com] Connecting to remote\u2026","rel":"","context":"In &quot;Technology&quot;","block_context":{"text":"Technology","link":"https:\/\/www.markwilson.co.uk\/blog\/topic\/technology"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.markwilson.co.uk\/blog\/images\/powershell-office365.png?resize=350%2C200&ssl=1","width":350,"height":200,"srcset":"https:\/\/i0.wp.com\/www.markwilson.co.uk\/blog\/images\/powershell-office365.png?resize=350%2C200&ssl=1 1x, https:\/\/i0.wp.com\/www.markwilson.co.uk\/blog\/images\/powershell-office365.png?resize=525%2C300&ssl=1 1.5x"},"classes":[]},{"id":6340,"url":"https:\/\/www.markwilson.co.uk\/blog\/2016\/04\/marks-office-365-resource-centre.htm","url_meta":{"origin":6130,"position":5},"title":"Retired: Mark&#8217;s Office 365 Resource Centre","author":"Mark Wilson","date":"Monday 18 April 2016","format":false,"excerpt":"18 months ago, I created \"Mark's\u00a0Office 365 Resource Centre\" using\u00a0the public site from my Office 365 subscription. Over the last few months it's fallen by the wayside as my focus has recently moved towards Azure (and Office 365 public websites are a deprecated feature) so I decided to move it\u2026","rel":"","context":"In &quot;Technology&quot;","block_context":{"text":"Technology","link":"https:\/\/www.markwilson.co.uk\/blog\/topic\/technology"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]}],"jetpack_sharing_enabled":true,"_links":{"self":[{"href":"https:\/\/www.markwilson.co.uk\/blog\/wp-json\/wp\/v2\/posts\/6130","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.markwilson.co.uk\/blog\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.markwilson.co.uk\/blog\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.markwilson.co.uk\/blog\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.markwilson.co.uk\/blog\/wp-json\/wp\/v2\/comments?post=6130"}],"version-history":[{"count":6,"href":"https:\/\/www.markwilson.co.uk\/blog\/wp-json\/wp\/v2\/posts\/6130\/revisions"}],"predecessor-version":[{"id":6170,"href":"https:\/\/www.markwilson.co.uk\/blog\/wp-json\/wp\/v2\/posts\/6130\/revisions\/6170"}],"wp:attachment":[{"href":"https:\/\/www.markwilson.co.uk\/blog\/wp-json\/wp\/v2\/media?parent=6130"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.markwilson.co.uk\/blog\/wp-json\/wp\/v2\/categories?post=6130"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.markwilson.co.uk\/blog\/wp-json\/wp\/v2\/tags?post=6130"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}