Life after Cherwell: How mid-market IT teams can survive (and win) before the 2026 deadline

Once Cherwell reaches end-of-life, your service desk, workflows, and integrations will be running on a platform that no longer receives updates or security patches. For IT managers, this creates important considerations around operational continuity and compliance requirements.  

This blog is for IT managers and IT leaders in mid-market organizations who: 

• Rely on Cherwell for day-to-day IT service delivery 
• Live in Microsoft 365 (Outlook, Teams, Entra ID, Intune, Azure) 
• Want a thoughtful transition away from Cherwell without disrupting operations
• Need a realistic way to move off Cherwell without a multi-year, big-bang project 

Here's what we recommend: Planning ahead gives you time to implement a solid solution before the transition deadline. One effective approach is moving to a Microsoft-native ITSM + ITAM platform like ALVAO, which can streamline your migration. Let's explore why this works and what your next steps could be.

What Cherwell’s end of life really means for you

When a vendor says “end of life”, it’s easy to think:  “We’ve got time. It will keep running. We’ll deal with it later.” 

Technically, yes - your Cherwell instance will not shut itself off on the deadline. But here’s what actually changes when it goes EoL: 

• No more security patches 
• No more bug fixes or maintenance 
• No new features or integrations 
• Support disappears entirely 

From an IT Manager or IT Director’s perspective, that looks like: 

• Growing security risk - you are running a core system that will not be patched for new vulnerabilities. 
• Compliance problems - auditors and frameworks increasingly expect supported software for critical systems. 
• Technical debt - every new tool you add must hook into an ageing platform with no future roadmap. 
• Skills risk - fewer people are willing to specialize in a “dead” tool, and every change feels more fragile.

It’s not about fear. It’s about risk balance.

IT teams that move early get to choose their replacement and migration plan on their own terms. Those that wait risk being pushed into a rushed decision when something breaks, a security incident hits, or an audit raises a red flag. 

Your real options after Cherwell 

Most Cherwell customers we speak with are looking at three basic routes: 

1. Move to the “official” successor in the same vendor family   

• Pro: some continuity, familiar vendor name, large portfolio.
• Con: often more complex and expensive than what mid-market teams really need. 

2. Jump to a large enterprise suite   

• Pro: huge ecosystem, lots of modules, big-brand comfort. 
• Con: long projects, heavy consulting, ongoing admin overhead – not always a great fit for a 500–5,000 employee organization. 

3. Choose a focused, Microsoft-native ITSM + ITAM platform   

• Pro: fits how your org works today (Microsoft 365), integrates deeply with Entra ID, Intune, Teams, Outlook, and gives you ITSM and ITAM in one. 
• Con: you may not know these platforms as well as the “big names” yet, so there’s some discovery to do.

If you live in Outlook and Teams, and your devices are in Intune or ConfigMgr, that third option is the most logical. 

That’s where ALVAO comes in. Check out the video.

Why mid-market IT managers are looking at ALVAO after Cherwell 

"The time frame was tight because we had other projects that couldn’t be moved, and the license for our old helpdesk was expiring in a few months. Despite the tight deadline, the integration and implementation went smoothly. Having a deadline really helped keep us on track. We had no choice but to go live on time, and we managed to do it with minimal downtime,“ says Mark Challis, IT Operations and Security Manager at EIP.

ALVAO is an ITSM and IT Asset Management platform built around Microsoft 365. 

Think of it as: “One place to handle requests, incidents, changes and assets, with your users and devices coming straight from Microsoft.”  

For a Cherwell customer, there are 4 reasons this matters. 

1. It’s Microsoft-native, not just “integrated” 

With ALVAO: 

• Microsoft look and feel providing quick and easy adoption. 
• Users raise and track tickets directly from Outlook and Teams. 
• Identity and access are governed in Entra ID. 
• Devices and policies come from Intune and other Microsoft tools. 
• ALVAO runs on Azure or on-premises, aligning with the strategy you already have. 

Instead of wiring a generic ITSM tool into Microsoft 365, you get a platform that was designed to live in that ecosystem from day one. 

2. ITSM + ITAM in one flow 

Cherwell often sits at the center while asset data lives all over the place - a bit in Cherwell, a bit in other tools, a bit in spreadsheets. 

In ALVAO: Service Desk and Asset Management are built together.

Every ticket can show you: 

• Which device is involved.
• Who owns it.
• Where it is.
• Its history, warranty, and risk status.

That makes life easier when: 

• You are troubleshooting issues. 
• You need to prove control of assets during audits. 
• You want to clean up unused software and reduce license spend.

3. Built for mid-market teams, not just huge enterprises 

ALVAO is designed for organizations that: 

• Require pinkVERIFY processes and governance.
• Don’t have the appetite (or budget) for multi-year-old platform programs.
• Need to be up and running in months, not years.

You get the capabilities you actually need: 

• Incident, request, change, problem, knowledge.
• Self-service portal and catalogues.
• CMDB / asset records and full lifecycle ITAM.
• Reporting and analytics (powered by Microsoft tools).

Without being forced into a massive, all-encompassing enterprise suite.

4. A migration story that doesn’t wreck your year 

Moving off Cherwell should not mean “freeze everything for 18 months”. 

With ALVAO, the recommended approach is phased: 

1. Assess your current Cherwell footprint: objects, workflows, integrations.   
2. Move core processes (like incident and requests) into ALVAO and start using the Microsoft-native experience.   
3. Expand and switch off Cherwell as you move the rest of your processes and data.

You can run the two systems side by side for a period, so: 

• Users and agents don’t feel a sudden shock. 
• Critical integrations have time to be rebuilt or replaced. 
• You don’t rely on a “big bang” weekend where everything has to work first time.

What a Cherwell to ALVAO migration looks like

Here is a simple picture you can show to your CIO or IT Director. 

Step 1: Assess and plan

• Inventory what you actually use in Cherwell (processes, objects, key integrations). 
• Identify where you are already heavily invested in Microsoft 365. 
• Agree on a realistic timeframe (often 12–18 months for a solid, controlled migration). 

What ALVAO can do here: Run a Cherwell EoL assessment workshop with you. Map your current state and show what each process would look like in ALVAO. 

Step 2: Modernize in parallel 

• Stand up ALVAO in your Microsoft 365 environment. 
• Implement priority processes there: incidents, service requests, asset records. 
• Let a pilot group start using ALVAO while Cherwell is still running. 

What ALVAO can do here: Provide best-practice templates and guidance so you are not rebuilding everything from scratch. Use standard integrations and data migration patterns. 

Step 3: Switch and optimize 

• Migrate remaining processes and data. 
• Train users and stakeholders in the new self-service and portal experiences. 
• Switch Cherwell to read-only or retire it completely before EoL.

What ALVAO can do here: Support your team through cutover and fine-tuning, then help you extend the platform to HR, Facilities, or other internal teams if you want to. 

What you risk by waiting 

If you are an IT Manager or ITSM lead, you are probably already busy enough. It is tempting to say: “Yes, we know about Cherwell EoL. We’ll look at it next year.” 

Here is the uncomfortable reality: 

• A serious platform change always takes time: selection, procurement, design, configuration, migration, rollout. 
• Your security and compliance team will increasingly push back on unsupported systems. 
• If something major breaks close to or after EoL, you won’t have vendor support to fall back on. 
• Your own personal risk rises the longer you knowingly run a critical, unsupported platform.

The worst-case scenario is not “we miss a feature”.  It’s “we are suddenly left with nothing reliable managing our requests, changes, and assets”. 

Starting now doesn’t mean you rip Cherwell out tomorrow.   

It means you: 

• Lock in budget and executive support. 
• Shortlist realistic successor platforms. 
• Build a migration path that fits your organization's pace.

What you can do this month 

If you are still on Cherwell and you know your organization lives in Microsoft 365, here is a simple action list: 

1. Acknowledge the EoL as a real risk  

• Bring it into your risk register. 
• Make sure your CIO, CISO, and Procurement are aware of the 2026 deadline.

2. Shortlist your replacement options   

• Include at least one Microsoft-native ITSM + ITAM platform (like ALVAO), not just giant suites. 
• Focus on time-to-value and fit for your org, not just brand names.

3. Book a Cherwell EoL call with ALVAO   

Use 30–60 minutes to: 

• Walk through your current set-up. 
• Understand how a phased Cherwell to ALVAO migration would look. 
• Get a rough scope and timeline so you can plan budget and internal resources. 

4. Get a live demo for your team   

Let your Service Desk, ITSM owners, and asset managers see: 

• Tickets in Outlook and Teams. 
• Asset data alongside requests. 
• How reporting and auditing would work post-Cherwell. 

Don’t wait until you have nothing solid left 

Cherwell’s end-of-life is not the end of your IT service management unless you let it be. 

You can turn this into an opportunity to: 

• Simplify your toolset 
• Align service management and assets in one place 
• Get more value from the Microsoft 365 investments you already have

ALVAO gives you a realistic, mid-market-friendly way to do that: 

• Microsoft-native ITSM + ITAM 
• Phased migration instead of big-bang chaos 
• A platform your team can actually own and evolve 

Ready to see what life after Cherwell looks like? 

If you want to survive the change before you are left with an unsupported system: 

• Book a call with ALVAO.  
• Discuss your current set-up, risks, and a realistic migration path. 
• Request an ALVAO demo. 
• See how a Microsoft-native ITSM + ITAM platform can replace Cherwell for your organization.

The 2026 deadline will not move.  

The question is whether you meet it on your terms with a platform ready to take over or wait until you are forced into a rushed decision. 

You don’t need to wait.   

Start that conversation today