Microsoft 365 vs. Windows Server

Overview
ProductRatingMost Used ByProduct SummaryStarting Price
Microsoft 365
Score 8.6 out of 10
N/A
Microsoft 365 (formerly Office 365) is a Microsoft Cloud subscription service that includes Microsoft Office products (Word, Excel, PowerPoint, OneNote, Outlook, Publisher, and Access). The software can be installed across multiple devices and ensures that users always have the most up-to-date version of the included Office applications.
$5
Per User Per Month
Windows Server
Score 8.5 out of 10
N/A
N/AN/A
Pricing
Microsoft 365Windows Server
Editions & Modules
Business Basic
$5.00
Per User Per Month
Individual
$5.84
*Per Month
Business - Apps
$8.25
Per User Per Month
Enterprise - F3
$10.00
Per User Per Month
Business Standard
$12.50
Per User Per Month
Business Premium
$20.00
Per User Per Month
Enterprise - E3
$32.00
Per User Per Month
Enterprise - E5
$57.00
Per User Per Month
No answers on this topic
Offerings
Pricing Offerings
Microsoft 365Windows Server
Free Trial
NoNo
Free/Freemium Version
NoNo
Premium Consulting/Integration Services
NoNo
Entry-level Setup FeeNo setup feeNo setup fee
Additional Details*When billed annually.
More Pricing Information
Community Pulse
Microsoft 365Windows Server
Considered Both Products
Microsoft 365
Chose Microsoft 365
It's still a Microsoft product, but the Online model is far superior to the on-prem offerings. Especially with Microsoft focusing on their online platform over their on-prem servers. Migration from these on-prem services is fairly simple and Microsoft has done a great job to …
Chose Microsoft 365
Microsoft's products are still the industry standard and most of our [other] software requires us to use Microsoft Office.
Windows Server
Chose Windows Server
Windows Server blows any of the Linux flavors I've used out of the water. Even after gaining experience with Linux, I'm able to achieve the same results in Windows Server from a command line much quicker than in Linux simply because Windows Server, especially with the …
Chose Windows Server
We have not really evaluated, nor used other servers OS's other than Windows Server. Since our environment is primarily Windows-based, with primarily Windows endpoints (and very few Mac or Linux endpoints), it has been the decision of the organization to use the Windows Server …
Chose Windows Server
There are plenty of other server solutions out there which may be better suited for certain tasks, but Windows Server is the way to get a Windows environment going. For simple setups, there are many alternatives, but often there are key features lacking, or a restriction on …
Chose Windows Server
Windows Server is by far the easiest server option to get started with because they offer the same kind of interface with windows that most users are already familiar with. Plus, it's the most graphically friendly option, so it is easy to navigate. Lastly, it is the most …
Chose Windows Server
We have used various flavors of Linux as it is the only other real competitor in the small to large business world. In most cases it is harder to find technical expertise in the Linux server world verse Windows Server. For this reason Windows has remained our go to operating …
Chose Windows Server
When using a Linux system such as CentOS in a server situation to get certain features like Windows Server, it can take a lot of jerry-rigging and configuration to get the same results that can be set up with Windows Server in a lower amount of time.
Chose Windows Server
Easy to use server operating system as compared to other operating systems (OS) which might require you to do a configuration via a terminal. Installation and managing of server - client applications are easy to use. Less load on server depending on the number of users …
Chose Windows Server
Windows Server allows much more control and flexibility than online file storage solutions. Windows is also much faster than cloud file storage and does not require the Internet. Greater flexibility and control means more time managing user that includes upgrading servers and …
Chose Windows Server
We have utilized Windows Server for over a decade and have not had a reason to look at any other server environment. Our vendors also specify that their applications will run best on a Windows Server environment and they have not been wrong with the ease of use it provides. …
Chose Windows Server
HP-UX is a great product, but it has a much higher learning curve than Windows server. Even if you're familiar with Linux/Unix, HP-UX will still be very challenging if you've never used it before. HP-UX commands can be different than even other Linux/Unix commands. Whereas …
Features
Microsoft 365Windows Server
Operating System
Comparison of Operating System features of Product A and Product B
Microsoft 365
-
Ratings
Windows Server
7.8
5 Ratings
8% below category average
File Management00 Ratings9.05 Ratings
Software Application Management00 Ratings8.05 Ratings
System Update Frequency00 Ratings6.65 Ratings
Operating System Security00 Ratings7.65 Ratings
Best Alternatives
Microsoft 365Windows Server
Small Businesses
Google Workspace
Google Workspace
Score 9.1 out of 10
Ubuntu
Ubuntu
Score 8.5 out of 10
Medium-sized Companies
Google Workspace
Google Workspace
Score 9.1 out of 10
Red Hat Enterprise Linux (RHEL)
Red Hat Enterprise Linux (RHEL)
Score 9.0 out of 10
Enterprises
Microsoft 365 Business Premium
Microsoft 365 Business Premium
Score 8.9 out of 10
Red Hat Enterprise Linux (RHEL)
Red Hat Enterprise Linux (RHEL)
Score 9.0 out of 10
All AlternativesView all alternativesView all alternatives
User Ratings
Microsoft 365Windows Server
Likelihood to Recommend
8.0
(242 ratings)
8.2
(63 ratings)
Likelihood to Renew
9.5
(6 ratings)
9.1
(6 ratings)
Usability
7.7
(13 ratings)
8.2
(7 ratings)
Availability
-
(0 ratings)
7.3
(1 ratings)
Performance
-
(0 ratings)
5.5
(1 ratings)
Support Rating
8.9
(54 ratings)
6.4
(19 ratings)
Implementation Rating
9.0
(2 ratings)
9.1
(4 ratings)
Configurability
-
(0 ratings)
9.1
(2 ratings)
Contract Terms and Pricing Model
-
(0 ratings)
4.5
(1 ratings)
Ease of integration
-
(0 ratings)
9.1
(1 ratings)
Product Scalability
-
(0 ratings)
9.1
(1 ratings)
Professional Services
-
(0 ratings)
6.4
(1 ratings)
Vendor post-sale
-
(0 ratings)
7.3
(1 ratings)
Vendor pre-sale
-
(0 ratings)
8.2
(1 ratings)
User Testimonials
Microsoft 365Windows Server
Likelihood to Recommend
Microsoft
Microsoft 365 would be well suited for medium to large enterprises. This is where there are several hundreds or thousands of people. Since most everyone has used one of the applications the learning curve would be reduced. Another reason would be the ability to implement security measures to prevent access to sensitive data. This could justify the cost of an Enterprise license.
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Microsoft
Windows Server and Active Directory is very robust and stable, it has been a staple in every IT environment I have worked in during my career. Junior to Intermediate admins can learn Windows Server easily, the user interfaces make administration tasks very easy as well as the documentation available through a vast amount of resources. There are other Operating Systems available with no GUI which has a smaller attack surface, faster update installation and reboot time. Windows Server does have the ability to remove the desktop experience, however it is not something I have had experience with and I believe most administrators choose not to remove it.
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Pros
Microsoft
  • Chat with teams and the integrations with the other apps, and many more smaller ones, like to-dos, news, and the recent Outlook integration.
  • Easy embedding on SharePoint to broadcast all the content created in the different tools.
  • The office package is still robust with the good things from the past and new additions.
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Microsoft
  • Backup of workstations & itself - reliably, consistently, with Bare-Metal Restore and deduplication
  • File management and Security on a per file/folder/user basis is simple and fully done through an easy GUI
  • DNS, DHCP server functions are easy to configure using the built-in GUI
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Cons
Microsoft
  • Forms lack comprehensive features and parameters for detailed questioning for example cannot be directly linked with Power BI
  • Outlook email filters are not handy to use and require more detailing in terms of location past emails
  • Teams requires substantially large amounts of system resources which could be finetuned
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Microsoft
  • Microsoft needs to minimize the update frequency by making the product more secure. It can become very exhausting trying to keep updated if you don't have a dedicated support team. It can become challenging where the business is unable to allow downtime for reboots as part of the update process.
  • Prone to security and audit vulnerabilities.
  • The operating system needs more CPU and memory resources compared to other options such as Linux.
  • Understanding the licensing model can be abit confusing.
  • Comes with a standard firewall, but not the most secured one available. Would suggest using a more secured firewall as part of your antivirus software.
  • Due to the number of vulnerabilities and the operating system being a target for hackers, anti-virus software is a must.
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Likelihood to Renew
Microsoft
So far the Microsoft 365 platform provides features and tools that can cater to 100% of present organizations needs considering both technical and business necessities, however most features are not been effectively utilised at present. The current featureset is able to cover for most of the future needs of the business and technical functions.
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Microsoft
I've carefully reviewed the servers and services currently running on Windows Server 2012, and given the opportunity would renew them as is going forward. There are two systems I currently have in place, one is a very large Linux implementation for a large ecommerce site, and one is a very large backup solution front ended by FTP servers running Linux. Neither are well suited for Windows, but the overall network infrastructure is and will be Windows Server for the foreseeable future.
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Usability
Microsoft
Microsoft 365 is the gold standard for performing project tasks in a professional environment, enabling the quick transfer and exchange of files and ideas for team members who work locally and remotely. Its suite of tools is familiar and has evolved to being cloud based, allowing for files to be updated in real time from near and far.
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Microsoft
Anyone new to IT could easily use the familiar Desktop Experience (GUI) version because we all know how to use Windows, whether a client or server version. Once an IT user is more comfortable with the operating system, they can move on to the Core version, which is the way to go in almost all situations.
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Reliability and Availability
Microsoft
To-date Microsoft 365 platform has offered an amazing uptime and availability percentage per year compared to all other products which provide the stability and overall business resilience of their ecosystem which is a great relief for information technology service entitites which heavy rely on Microsoft offerings as a whole to redeliver their own custom products
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Microsoft
some times server hungs and user sessions were busy to connect
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Performance
Microsoft
The Microsoft 365 tools expects and demands a substantial amount of system resources to operate at optimal level and even more when integrated with other applications which is a downside, however given that external supporting tech factors such as fibre/broadband speed bandwidth, high speed RAM and ample storage resources are allocated the tools work error free providing robust communication
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Microsoft
need to improve the performance more
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Support Rating
Microsoft
Over the past 8 years of using Microsoft 365, I have noticed that they change vendors often. This always leads to a poor experience in the beginning, then levels out after some time for the company to get things worked out. As a customer, it is really frustrating because I don't have time when something isn't working to have them "look into my issue" and get back with me. They have even closed a ticket I specifically told them to keep open. Your applications are only as good as the support.
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Microsoft
Microsoft's support is hugely wide-ranging from articles online to having to contact them directly for the more serious issues. In recent years when I have contacted them directly, I have found the support o be excellent as I have found myself connected to very knowledgeable people in the field in which I needed the support. The online support available is vast and I tend to find most of the time that there is always someone out there who has had the same issue as me in the past and knows something about how to resolve it! This is the advantage of using industry standard and long-established systems such as Windows Server.
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In-Person Training
Microsoft
The resellers involved with selling Microsoft products are reluctant to provide in person specialist trainings to consumers due to the fact of costs of economies of scale and is not provided free of charge most of the time. In Person trainings needs to be agreed to at the initiation of projects and implementations for better ROI.
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Microsoft
it was my senior who trained Windows Server features and i was satisfied
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Online Training
Microsoft
The standard training offered with 3rd part resellers are fairly standard and covers the basic workability however the trainings needs to be specifically customised according to unique requirements of the organizations. for example an MSP would need to master specific communications verticals within Microsoft 365 whereas and online store using Microsoft 365 would needs to master a different set of tools within the suite to get the best ROI post implementation.
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Microsoft
it was recorded session and useful
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Implementation Rating
Microsoft
The Microsoft support partners are more than capable of handling implementations and dealing with unprecedented errors during the implementations. Not part of the implementation though the setup was done with minimum misconfigurations which is evident with present live setup which works fine without any bugs and gaps at present context.
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Microsoft
Make sure that you have detailed processes in place for every server instance you plan to install/upgrade, if possible get the base OS loaded and Windows Updates applied ahead of time, and if using a VM take a snapshot prior to installing each role, as well as along the way.
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Alternatives Considered
Microsoft
Typically I prefer working with companies with Microsoft 365 as their main tool because they're usually a fast growing company with a global presence. I like using it for work because it's easy to collaborate, share, review, comment, reply in any of the tools. The mobile app for Outlook and Teams are lifesavers when we're constantly traveling and you can join meetings on the mobile Teams to never miss a beat.
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Microsoft
They are different experiences, and while the other solutions offer enterprise-grade stability and, in some cases, address Windows server shortcomings (such as patching), they all do the trick, but the other solutions require a deeper technical background/configuration of items at the command line, which some people are not fully comfortable with.
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Contract Terms and Pricing Model
Microsoft
Microsoft pricing is not very expensive and yet not very cheap as well, and it hovers in between the baseline. The charges are mostly based on the tier level partners who charge based on their individual reputation in the market. Power negotiation will lead to cost effective and attractive pricing
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Microsoft
need to reduce a lot
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Scalability
Microsoft
Multiple tools within the same platform have been deployed successfully within different functional technical and non technical teams such as Devops, SOC, NOC, Shared services, Managed services, Global Information technology, Cloud operations, Finance, Administration, human resources and all these teams collaborate while maintaining central uniformity in terms of global standards who are dispersed in different geographical locations with ease
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Microsoft
yes i completely agree multi deployment
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Professional Services
Microsoft
Have not directly obtained professional services from Microsoft but rather obtained specialized services such as implementations and configurations, setting up and integration support with Microsoft authorized suppliers, 3rd parties, and resellers, which has been a pleasant experience. Again the level of delivery quality on professional services is based on the level of hands on exposure of the 3rd party
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Microsoft
i like the professional service but need to improve
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Return on Investment
Microsoft
  • We have a lot of nonprofit users, so they have a good ROI.
  • I like the constant updates without having to purchase the software repeatedly.
  • I used to purchase each Office (insert year here) often, so the software was up to date and had the newest options and connectors. I think my return on investment would have been much better if Microsoft had updated those versions to keep them current; after all, we did pay for them.
  • Microsoft 365's offering a monthly fee or a discount for a year helps, and you can look at it as a free backup if you have everything set to back up to One Drive. (Cloud-based document filing you can access anywhere ( with an internet connection)—you Can't beat that!)
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Microsoft
  • Ability to keep all files in one place and give access to users makes file management easy to control.
  • VPN Access to off-site users is a plus.
  • Secure access to on-site SQL data from our accounting and estimating data is a plus.
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ScreenShots