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How to approach updates on Guidewire Cloud – from release cadence to adoption
Jan 13, 2026 Cloud, Guidewire , Article , Core System Implementation

Guidewire regularly releases new versions of its cloud-based insurance core system. Guidewire names these Guidewire Cloud releases after ski resorts and are often referred to as “Guidewire ski releases.” Guidewire typically delivers several updates per year. Below I share a few practical thoughts on how insurance companies can approach updates to support business value while keeping risk under control.

The impact of Guidewire Cloud updates

Guidewire Cloud updates can provide insurance companies with significant value by introducing new features and improvements across the platform. Depending on the release, these enhancements may relate to underwriting and rules, APIs for core operations, and stronger analytics and data capabilities across areas such as claims and pricing. The key is to treat each update as an opportunity to adopt valuable improvements – without causing unnecessary disruption to ongoing business initiatives.

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How often should you update Guidewire Cloud

In general, insurance companies using Guidewire are recommended to update regularly. The more frequently an insurer updates, the less risky each update will be, simply because there are fewer changes will need to be absorbed. However, efficiency is also a factor to consider. While insurers should prepare for regular releases in Guidewire Cloud, they should not become overly dependent on a fixed schedule.

 

A company that updates with every new release of the Cloud version of Guidewire will require more time from its team. With so many opportunities and changes in insurance IT, this has become an important point to consider. So why should a company update to a newer Guidewire Cloud release now?

 

There are three simple answers to this:

 

  • If an insurer is more than two versions behind, it seems that it shouldn’t hesitate and should catch up with fixes and improvements
  • The newest release contains the features required by the insurer
  • The insurer’s team has the capacity to do so

As with many other software solutions, it is advisable to do some research before deciding whether to follow an update. There should be a dedicated team in your company that investigates and tests each release before you decide whether you will update to the latest available release or wait for the subsequent ones. If the timing is right and your team has the capacity, now could be the ideal time to invest in learning how to update without difficulty.

How to explore new features of Guidewire Cloud

If the answer to all these three points is no, I would recommend skipping this update and preparing for the next. Guidewire Cloud Platform makes it easier for insurance companies to innovate than a self-managed version. Updates do not require the same level of operational effort as traditional upgrades, production disruption is usually shorter, and many improvements can be adopted without large-scale changes to the surrounding landscape. However, if your company is completing a major initiative that could be delayed by an update, it might be advisable to wait.

 

Time is an important factor, and it makes sense to start evaluating an update soon after it is released. If another release is expected relatively soon, it is more efficient to coordinate your efforts and avoid updating twice in a quick succession. You should avoid completing an update just before – or only shortly after – the next release becomes available.

 

Guidewire offers interesting improvements with each new release, and it might be the case that a new release introduces capabilities an insurer has built through customisation in the past. I recommend testing and comparing new out-of-the-box functionality with the existing solution. If what’s being released is mature enough and covers what your company needs (and potentially more), adopt it. It cannot be repeated often enough: think twice before you customise and deviate from the out-of-the-box version of the system. Every customisation increases maintenance effort and makes future updates more difficult.

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Update independently if your company is prepared

Updates should be planned ambitiously, but realistically. From our experience, there can be significant differences in the complexity, effort, and time required for an update. It depends on:

 

  • How close to out-of-the-box (OOTB) a company is with its system
  • How much it was configured and how much it was customized
  • How many versions the current version is behind
  • How stable the current version runs
  • How much testing is automated

Insurers should rely on Guidewire for the heavy lifting where it is provided as part of the cloud service, and focus their own effort on validation and adoption. If you have enough capacity in your team and you are prepared well, you can approach updates independently. If done properly, the organisation will be able to repeat this process faster with the next release.

 

But what does properly mean? The team should prepare an internal update procedure with a clear division of responsibilities that can be reused for every future update. They should also have an automated regression test pack in place and keep the test coverage matrix and test cases updated, including an execution plan and representative test data.

Authors of the article

 

photo of article author     Tomasz Turowski - IT Manager, North America