10 TOP OFFICE 365 MIGRATION CHALLENGES - Priasoft

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The Experts inExchange Migration 10THE TOPOFFICE 365MIGRATIONCHALLENGESExplore the top challenges and risks you will face during an Exchangemigration to Office 365. This is a must read for all IT professionalsthat are planning or conducting a migration project to Office 365.

IntroductionThere are many benefits to moving to Office 365 but it iscritically important that you evaluate both the current andfuture needs of your business. Switching is never easy. Theexperts at Priasoft have developed this helpful guidebook todiscuss the main challenges that you will be presented whenmigrating your Exchange email to Office 365. It will help youunderstand risks, potential issues and technology impact ofnavigating a complex migration project while providing insighton designing a successful migration process for your business.introduction

CHALLENGE 1Tenant Typeand OfferingOne of the first decisions that has to be made after committing to Office365 is which plan to select.Currently, there are 6 main categories of service plans totaling over 20 unique plan offerings. With somany options, it is important to make a proper selection and one that considers both current needsand scope and also the likely growth of the organization over time.Office365 Service Plan Categories: Personal/Home Small Business Enterprise Government Education ITAR and DedicatedMaking things even more complicated is the ability to only subscribe to Exchange Online. Thisoffering, while less expensive only provides access to Microsoft’s hosted email solution – SharePoint,Skype, and many of the other features of Office365 are not included.It can be frustrating in the future to find that one cannot switch from one service plan to another andthat a migration is required. Some plans can simply be “upgraded” while other cannot. There aremany subtle parameters that allow switching and upgrading, many which are not obvious and are notdiscovered until an actual attempt is made to switch.Microsoft is consistently changing the service plan structure to adapt to market demands and revenueand profit pressures. It is very wise to evaluate your business properly and to hedge for any possibilitywhere switching plans may be necessary in the future, and to avoid that case by moving into a largerthan-needed-for-now plan.page 2

CHALLENGE1Tenant Type and OfferingPersonal and Home PlansEducation Plansexample from a small business plan to an enterprise plan,These plans are for individuals, independent professionals,Office365 has separate and distinct offerings from educationis much like changing to a new hosting provider and all theand small businesses that consist of only a few people. Thereinstitutions and organizations. The value of some of thesecomplexities that go with it.are versions of these plans that can include the full Officeplans is reduced cost, free mailboxes for students and alumni,product suite (Outlook, Word, Excel, etc.) or can be “web only”and education focused tools and support. As with all the otherThis is especially important for the small business plans thatversions. There is no ability to simply “switch” from thesecategories, this plan has several offerings for different sizelimit user counts to 300 or less. If an organization, at the timeplans to any business plan.entities.of selection of the plan, choose the small business plan andSmall Business PlansITAR and Dedicated Plansexceed that limit, 2 migrations would be necessary: one fromThese plans are for small businesses ranging from a fewThese plans are not discussed very often and Microsoft doesthe small business plan to an enterprise plan, and anotherdozen employees up to 300 employees (as of 2015). There arenot actively promote these plans as they are very specializedmigration from the acquired company to the enterprise plan.several plans offerings in this category with different softwareand niche. However, for some organizations, especially ITARThis challenge is exacerbated if the acquired company is alsoand service options. Not all offerings in this category includeorganizations, this may be the only option if you are lookingon Office365 due to lack of tools in the industry for tenant-to-Microsoft Exchange.for a trusted Cloud platform. Microsoft has had dedicatedtenant migrations.later acquires another company that would cause them tohosting plans for many years (it used to be called BPOS-D).Enterprise PlansDedicated plans are often more expensive as they entail theThese plans are for mid and large size organizations. Theyuse of completely segregated computing resources such thatsupport an unlimited number of users, hybrid-modedata in a dedicated platform does not commingle with thedeployments, and most enterprise-class features that wouldmulti-tenant offerings. Dedicated plans have better supportbe expected.for customization and approved 3rd party integrations. Dueto the costs, these plans are often only justifiable for very largeGovernment Plansorganizations.There also exist several offerings specifically tailored forFederal, State, and Local Government institutions andUnseen Challengesagencies. These plans offer certified compliance with specificAs an organization grows, or shrinks if that is the case,rules and laws and ensure that data is not stored out of thethere may be a need to change the Office365 plan to bettercountry in any way. There are sometimes the need to makeaccommodate the size of the organization or to better controlspecific requests for certain compliance, like CJIS or HIPPA inthe spending on the service. The challenge is that, while thereorder to get a certificate that proves the entity is compliant.is some ability to mix different offerings within a category,The data for government entities is segmented away fromthere are partitions between the different categories. Thesethe normal multi-tenant data of the general Office365partitions create a situation that requires a migration in orderenvironment which ensures that government data is in no wayto change plans. Microsoft doesn’t currently provide supportcommingled with non-government data.for cross-tenant migration tasks. Changing categories, forPriasoft Migration Suite for Exchange 6.5 is the leading Microsoft Exchange migrationsolution that provides class leading flexibility, ease of use and performance.Learn more atpriasoft.compage 3

CHALLENGE 2Geo-locationof DataThe next topic of importance with considering a migration to Office365 is “where will the data belocated?” This can have subtle and obvious consequences. By the nature of Microsoft’s Cloud offering,a customer’s primary datacenter will be based on information provide during the signup process.The challenge here can be that if your organization is highly distributed, across many time zones orcountries, some users may get a better experience than others. Microsoft does not currently supportany model that lets an administrator have a tenant span multiple geographic locations. While it is truethat data protection exists in Office365 by replicating to 2 or more other datacenters, that only existsfor failover cases. A tenant admin doesn’t have the ability to dictate or influence the redundancy andusers will not connect to those replicated datacenters.The issue is most particularly felt when users span countries and the physical distance alone causeshigh latency. Outlook in particular, even with cached-mode enabled, behaves differently in a highlylatent setting than it does when on LAN or low latent networks.This issue is further complicated if your organization has any governmental requirement produceand keep data “in country”. A distributed organization would then likely require multiple Office365tenants, one for each country that has the requirement. This setup immediately leads to complexitiesand collaboration issues that are not apparent. Imagine needing to provide access to a sharedmailbox between tenants.The determination of how a client connects to Office365 is a bit of fuzzy science. When a request ismade, for example to ‘outlook.office365.com’, a DNS query is made to get an IP address for the name.However, since the name ‘outlook.office365.com’ is a generic name used world-wide, it is importantthat the IP address returned for the name be a close to the requester as possible. Microsoft hasimplemented a complex system that, in most cases, the results of a DNS query are returned with themost likely data center IP addresses.page 4

CHALLENGE2Geo-location of DataThis is not a strict science because there is not a centralshould place the connection to the nearest physical Microsoftsame email domain active on 2 tenants – so that means thatregistry of IP addresses and their physical location on thedatacenter. However, if the public DNS server is unknowntemporarily, the new tenant will need a different email domainearth. One could buy or lease a few public IPs from an ISP andby Microsoft, or if the exit to Internet for a company isuntil the migration completes and the old tenant is removed.the “record of ownership” might list the location, but there’sthrough a private connection to another location, the CNAMEnothing that requires that those IP addresses be used in atmay not be the closest. For example, a query of ‘outlook.This situation can also occur in a more natural case. Considerthat location in the record – they can be used anywhere in theoffice365.com’ may return ‘outlook-emeasouth.office365.a situation where a business decides to relocate to a differentworld. In the end, admins and architects should spend timecom’. However, if the physical location of the client or serverregion. There is no ability to simply change the tenant detailsto see what IPs and CNAME records are returned by DNS inmaking the connection is in the USA, this is a horrible result.with regards to that change. Users will change from beingtheir local region for the many common Office365 hostnames.These statements are being made here because testing andnear the datacenter to possibly being very far away from it,Some common names are:field results from other customers have shown that this exactincreasing the network latency in the process.scenario can happen. Outlook.office365.com (used by Outlook) Autodiscover.outlook.com and autodiscover-s.outlook.Each regional name, like ‘outlook-emeasouth.office365.com’,com (used by many tools and applications)is served by Round-Robin DNS – a feature of DNS that, upon Portal.office.com (used by web browsers)each new request, will reorder the IP addresses for the name. Ps.outlook.com (used by PowerShell)This provides a simple way to provide connection balancing ProvisioningApi.microsoftonline.com (used by AzureADacross several IP addresses. However, and especially whenpowershell)performance is important, not all of the IP addresses for aregional name will have the same responsiveness. It is wiseThe exercise may show that inconsistent results are returned,to ping and develop latency numbers for each IP address insuch that each new DNS query responds with a differentthe likely nearest datacenter hostname. One can then lockregional endpoint. If this is not corrected, this can lead toin the use of one of the IP addresses by the use of a “hosts”sporadic performance results where in one operation thingsfile (works for a single computer) or by adding the name inare responsive and smooth, but in another are very slowthe organization’s local DNS, possibly providing Round-Robinand faced with timeouts. Priasoft maintains list of world-features for only a few of the IPs; the ones with the lowestwide, dynamically discovered regional endpoints for ‘outlook.consistent latency.office365.com’ that you can view here at Worldwide Office365Endpoints.Lastly, once a tenant is created, the location cannot bechanged. If the location chosen during setup was doneWhen a lookup is performed for ‘outlook.office365.com’, theincorrectly, there is no choice except to create a new tenant,public DNS server on the Internet that makes the query iswith a different name, migrate from the old to the new, andused as a hint to determine a regional specific CNAME recordremove the old tenant. Then finally rename the tenant.for the generic ‘outlook.office365.com’ name. Ideally thisHowever, as simple as that may seem, one cannot have thePriasoft Migration Suite for Exchange 6.5 is the leading Microsoft Exchange migrationsolution that provides class leading flexibility, ease of use and performance.Learn more atpriasoft.comLearn more atpriasoft.compage 5

CHALLENGE 3EmailClientsOffice365’s email service is based, currently, on Microsoft Exchange 2013. As such, only certainmail clients will work with this service. It is important then to understand the full distribution oftypes and versions of the various email clients that exist in the organization. Failure to fully cataloghow the business will connect with Office365 can mean that some users cannot get mail, or thatsome applications – that depend on a specific version of Outlook, for example – may not work withOffice365.Microsoft Outlook, being the primary client most organizations use to access email and to collaboratewith other users, is of special importance. While Office365’s Exchange platform is based on Exchange2013, that will not be true forever. Work has already started to move tenants to the next wave ofExchange – Exchange 2016. Exchange 2013, and therefore Office365 as well, supports Outlook clientconnections from Office 2007 and later, with appropriate service packs and roll ups. However, it islikely to be a case where tenants that are created or transitioned to the next wave of Exchange findthat Outlook 2007 will no longer connect.Microsoft attempts to make this an easy decision by offering in most plans the inclusion of the Officesuite, which includes Outlook. Currently the office suite is Office 2013, but in the near future Office2016 will be available and nearly forced as the version to use. However, there are many differencesbetween prior versions of Outlook and Office and Office 2013. Some of the differences are obviouswhile many are subtle or nearly invisible. In a larger organization, training then becomes a potentiallyunseen cost with a transition to Office365. The visual differences alone between Office 2007 and 2013are stark enough that many users feel lost as to how to do certain things. Failure to provide trainingto end users means that help desk calls are likely to go up and user productivity to go down.page 6

CHALLENGE3Email ClientsThe subtle differences are also many, the most disruptingcalled “migrated code”. The meaning here is that when anin the profile, it will attempt to make a connection with thebeing the way that cached-mode works in Outlook 2013.organization transitions to Office365, such is very much likeserver, even if it has no need for its services. TCP times on theMicrosoft added a new feature – albeit a very good one – toa cross-forest migration scenario. Outlook does have thenetwork can range from a few seconds to 1 minute or more,control the size of the offline mailbox copy based on a dateability to detect when a mailbox moves to another Exchangedepending upon settings.range. One can specify that only the last 12 months of datadatabase, but only within the same Exchange Org deploymentbe stored locally and any other data is to be retrieved from– meaning within the same AD Forest.the server directly. This great feature though required aCustomers and consultants may claim that Hybrid-Modesolves this issue, but such is not actually true. Hybrid mode,completely new file format and one that is incompatibleOutlook, especially older versions, store detail in itsby design, forces the on-premises resources to remain alivewith the previous versions. Deployment of Office 2013configuration settings – called an Outlook Profile – that pointand active. However, as the business progresses in time, thethen must take into consideration the fact that users will beat Domain Controllers, Global Catalogs, and Exchange serversolder on-premises resource will likely be replaced or removed,required to download their mail from the server once again.from the environment in which it was first created. There is aeven if Hybrid-Mode will be maintained. When those eventsIf users are already at a distance from the current Exchangelarge misleading idea that a service – AutoDiscover – providedoccur, Outlook will begin having problems.platform (whether that is an on-premises or cloud platform isby Exchange (including Office365) will somehow fix this. Theirrelevant), the download of mail may take minutes or hours,AutoDiscover service is nothing more than an informationOthers may say that upgrading to Office 2013 will somehowdepending upon how many items are to be synchronized. Thisservice; it provides information about a user, nothing more.take care of this. This is also not exactly true. If Outlookissue is made worse if the change to Office 2013 is made after2007, for example, is replaced with Outlook 2013 through anmigrating to Office365 – the download of the users mail wouldOutlook uses this service to get current connection points andupgrade, Outlook will continue to use the profile that Outlookthen be done over the internet and a highly latent network.URLs for the various services that are provided by Microsoft2007 was using, including all the pointers to legacy resources.Exchange. However, when a pre-existing Outlook profileOutlook Web Access is another dramatic change from prioris simply “repointed” to another environment, it does notIt is imperative then to consider how the Outlook profiles forversions. So much so that training is quite necessary forattempt to detect if the change was simply a database change,end users will be managed. Failure to use a tool or processmany of the collaborative features. There has also been aor a cross-forest/cross-premises change. As such, Outlook willthat specifically addresses profiles means that issues arerecent trend to shift users of certain criteria – mail consumers,simply try to use the new connection points returned fromsimply waiting in the dark and will arise at some later date, in afor example, versus mail producers – to convert from usingAutoDiscover – it does no cleanup of the old, on-premisesvery uncontrolled fashion.Outlook to using OWA. This trend is based on cost savings assettings that exist in the profile.there are plans in Office365 that only provide OWA access forless per user than a full suite plan. Companies can actuallyThe results then are mixed and intermittent. For some users,mix plans together in one tenant – as long as they are in thethere appears to be no issue. For others, Outlook locks upsame category.intermittently or takes an unusual amount of time to startup, when first launched. When the source environmentThe use of Outlook also presents another issue that is evenresources, for which the Outlook profile has pointers, goesmore subtle, but extremely important. The issue is theoffline or is finally removed from use, Outlook will start tofact that Outlook does not have code built-in that would belock up. The reason is that while those settings still existPriasoft Migration Suite for Exchange 6.5 is the leading Microsoft Exchange migrationsolution that provides class leading flexibility, ease of use and performance.Learn more atpriasoft.compage 7

CHALLENGE 4Applications, Devicesand Services (A/D/S)Office365, by the nature of the service, is restrictive with regards to A/D/S and how those mightinteract with Exchange and email. It is important then to analyze the current environment to try anddiscover what applications, devices, or services might be integrated or dependent upon the emailsystem.For cases where these things are deeply integrated, it may not be possible for them to work withOffice365. Some examples of deep integration are:The use of an application mailbox.In this case, the application likely logs on directly to this mailbox and uses the same to send andreceive mail. Help desk applications very commonly are implemented in this way.The challengethen is configuring the application or service to use a mailbox in Office365. Currently, and for theforeseeable future, access to mailboxes in Office365 require the use of Outlook Anywhere (an HTTPSconnection mechanism). Unless the application or service is up to date, it may not be able to makesuch a connection. For example, there are several applications that depend upon Outlook 2003 – suchapplications will not work with Office365 while that dependency exists. Also remember that when thenext wave of Exchange is deployed internal to Microsoft, Outlook 2007 may drop from support – anyapplication depending specifically on Outlook 2007 may be an issue in the future.System Privileges and Admin AccessIn an on-premises deployment, it is possible to setup a service account that has broad access toall mailboxes in a database, all databases on a server, or all databases for the entire organization.Blackberry Enterprise Server (BES) was well known for this approach.There is no ability to have a permissions model like this in Office365. Applications that depend upona single account having broad access will likely not work and cannot be forced to work in this way.System Privilege is a special access mechanism in which an application can access Exchange datawith an elevated privilege level that ignores user permissions. For example, system privilege allowsan account to access the entire Public Folder tree in an organization, regardless of individual folderpermissions set by users or administrators – this is the same level of access that most Exchange servicespage 8

CHALLENGE4Applications, Devices and Servicesuse like Hub Transport, System Attendant, and many others.Office365 mailboxes have the settings needed.the vendor’s support team for details on Office365 support,and more importantly, how to transition from on-premises toDirect access to Active DirectoryCustom Address SchemesOffice365. This latter question is important because a productMany A/D/S are configured to work via LDAP with the localSome A/D/S use custom address types and either a transportmay support Office365 for new installations, but may not haveActive Directory environment. There is no LDAP access torule, custom gateway, or custom receive connector to facilitateany tools or feature for transitioning, possibly meaning muchinformation in Office365. A/D/S that depend on LDAP simplythe routing of such emails. For example, faxing solutions ofmanual work to reconfigure.won’t work with Office365 directly and this may force theuse a custom address type (non-SMTP) to handle routing.organization to use Hybrid-Mode.However, Office365 does not support custom address typeLastly, there may be client add-ins for Outlook that dependsend connectors like an on-premises deployment.on things that are expected to be available in an on-Transport RulesAdditionally, it is important to select a migration solution thatpremises deployment but which don’t exist with Office365Some A/D/S are setup and configured to use one or moreWILL migrate all the source email addresses, even if some are– for example, Active Directory. A survey from users andExchange Transport Rules, or are dependent upon the samenot SMTP (again, like a faxing solution), however in order todepartment leaders is prudent to capture how users interactto direct mail towards itself. Office365 does support transporthave routing work based on those custom address types, awith Exchange. It may be found that there are add-ins that arerules, but not necessarily with the same level of feature astransport rule may be necessary.either 3rd party or are created internally to support some LOBon-premises. This is especially important if the on-premisesapplication, service, or process. Failure to discover and apply atransport rule depends upon some local service, API, or filesetLocally Accessible Data or Servicestransitional path to such things can cause much frustration theon the Exchange server – there is no ability to customize theSome A/D/S require the install of a service, application, orday after a migration to Office365 or, potentially worse, failureExchange server implementation in Office365.libraries directly on an Exchange server, or on a memberto collect revenue if an add-in is specifically related to such anAt a minimum, there will be need to recreate the transportserver in the same domain as Exchange. Office365 providesactivity.rules and depending upon the complexity of the rule, mayno ability to modify the servers hosting exchange. Foror may not be able to support the A/D/S that uses it. Lastly,applications like this, it may be necessary to look for a newernot all service plans include the ability to create and manageversion of the product that specifically supports Office365, or atransport rules. Be sure to pick the right service plan if adifferent product entirely.discovery is made that requires the use of transport rules.For products that require a host in the same domain asPOP3 and IMAPExchange, the same issue exists in that there is no ability toSome A/D/S are only able to work with less rich Internetintegrate with the hosted environment in Office365 in such aprotocols. In Office365 POP3 and IMAP are supported,way as to add member servers or the like.but have to be set on a per-mailbox basis. If the choice ofOutside of A/D/S that have deep integration, there maymigration tools do not carry forward the source mailbox’sbe products used by an organization that are indirectlysetting it will need to be set manually aftewards. Or, if thesedependent upon the on-premises organization. In thosesettings were set by a policy in the on-premises environment,cases, it may be as simple as reconfiguring the product tomanual work will likely be needed to ensure that the newpoint to services at Office365 (POP, IMAP, etc.). Check withPriasoft Migration Suite for Exchange 6.5 is the leading Microsoft Exchange migrationsolution that provides class leading flexibility, ease of use and performance.Learn more atpriasoft.compage 9

CHALLENGE 5MigrationPerformanceDue to the fact that most on-premises deployments of Exchange will be at some physical distance fromMicrosoft’s Office365 datacenters, there is an inherent limiter to speed at which a migration can occur.Network latency is a frustrating reality that affects all migrations – on-premises and cloud alike. The issueis due to the nature of how data is stored in Exchange and how it is accessed.The core of the issue is not how much data there is, but how many items there are to be migrated.Consider 2 mailboxes of the same exact size: 500 MB for each mailbox. However, Mailbox-1 has 5000items in total, but Mailbox-2 has 15,000 items – the second mailbox will take nearly 3x longer to migratedue to the item count. This issue is compounded by network latency.Network LatencyLatency is simply a delay on the network waiting for electrons or photons to flow down a cable. Thegreater the distance the longer the delay. If the organization’s on-premises datacenter is 2000 miles awayfrom the nearest Office365 datacenter, there will be high latency over that distance. Adding to this issueis the possibility for poor network routing that artificially increases latency by routing data over a muchgreater distance than necessary. Consider a case where, in order to reach the nearest MS datacenter,data is sent from the on-premises datacenter, to another state, timezone, or even a country. Looking athow data is routed may show that it would be better to bypass that route, for specific destinations (likethe MS datacenter) and have it go directly from the on-premises datacenter to the MS datacenter.The impact of latency is quite important to understand as it affects ALL TOOLS and applications, includingOutlook clients. In any given application that needs to request and receive data from a remote server,there is the network protocol underneath that makes it all work, primarily TCP. Stateful connections likeTCP (of which HTTP is built on) have a series of short back and forth conversations before real data startsto flow, a sort of handshake that allows each side to know what is about to happen and when it ends.Latency causes the delay to be felt before and after each transmission of data.In the case of Exchange, this delay is felt on each side of an item copy. There’s a delay just before the itemis copied, and then at the end when the item copy completes. If the latency between the on-premisesmailbox and the Office365 mailbox is 50ms, and the mailbox has 10,000 items to be migrated, at apage 10

CHALLENGE5Migration Performanceminimum there will be 500,000ms of just waiting around,Another subtle consideration of very large item counts isthrottled. However, all throttling is based on authentication.which equals over 8 minutes of doing nothing. However,the impact they have on Exchange servers, especially olderIf the same account is used to do multiple, concurrentaccessing data in Exchange is not so simple. Items inversions. When a request to access a folder’s contents isoperations, throttling is quickly found and operations areexchange, whether they be a folder, message, contact,made, Exchange must reserve memory to hold the table ofeither block or delayed (aka tar-pitting). This effect should becalendar, or some other object type, are not files – they are notitems as a list for the requester. This creates a sort of “tableanalyzed both with tool selection for migration AND any otherstored as a row-of-bytes in a database. Each item is a table ofsession” for clients and tools. However, when the list is very3rd party A/S/D for which performance or concurrency play aproperties, possibly with sub-tables of other properties (likelarge, it can consume considerable RAM on the Exchangerole. One side effect that can happen is that a 3rd party LOBthe recipient list and attachment list on an item). There is

Exchange Migration OFFICE 365 MIGRATION . This is a must read for all IT professionals that are planning or conducting a migration project to Office 365. 10THE TOP. Introduction There are many benefits to moving to Office 365 but it is . the small business plan to an enterprise plan, and another migration from the acquired company to the .

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