Jira Admins: What’s your biggest challenge right now?

[Arkadiusz Wroblewski]

If you’re a Jira Admin in 2026, you’re probably juggling a mix of platform changes, team expectations, and “please fix this yesterday” requests. I’m curious what’s hitting hardest for others right now.

Here are a few common buckets I keep running into tell me which one is your #1 (or add your own):

1) Keeping Jira usable without becoming the “Jira Police”

How do you set standards (work item quality, statuses, naming, hygiene) without turning Jira into bureaucracy?

2) Cloud change fatigue and reliability wobbles

How are you coping with frequent changes, occasional performance issues, and the constant “is it us or Atlassian?” debugging?

3) Automation: powerful, but not always flexible

Where do you feel limited? service limits, targeting issues, cross-project logic, Assets integrations, etc.? And when do you decide it’s time for ScriptRunner/app support?

4) Reporting: everyone wants dashboards, nobody agrees on definitions

What’s the hardest part for you: data quality, consistent fields, cross-team reporting, leadership KPIs, or just getting people to trust the numbers?

5) Configuration sprawl

Team-managed vs company-managed, custom fields explosion, workflows that grew over years… what are you doing to stop Jira from becoming a maze?

6) Access, permissions, and “why can’t I see this?”

Still one of the most common ticket types. Any tips or best practices that actually reduced noise?

My honest take

For me, the hardest part is finding the balance between flexibility and consistency. Teams want Jira to fit how they work  but if everyone does their own thing, reporting and cross-team visibility fall apart. Jira setup is always a bit of an art, and keeping it useful without over-engineering is the constant challenge.

Over to you: What’s your biggest challenge right now and what’s one thing (process or platform) that would make your life easier?

[Sonal Nagpal]

Great question — this is very real.

If I had to pick one, it’s #5: Configuration sprawl.

After a few years, Jira becomes a collection of:

• Custom fields created “just in case”
• Slightly modified workflow clones
• Team-managed projects multiplying
• Automations stacked on automations

The hard part isn’t cleaning it up — it’s doing it without becoming the “Jira Police.”

What’s helped me:

• Standardize only what affects reporting (statuses, key fields, definitions)
• Add a lightweight review process before creating new fields/workflows
• Stop over-stretching native automation for cross-system logic

For example, instead of building complex automations to sync support tickets with engineering (especially across instances), we tried Sinergify from the Atlassian Marketplace, to connect Jira with Salesforce. From a Jira admin perspective, what worked was:

• Field-level sync control
• No forced workflow standardization
• Fewer duplicate tickets
• Less brittle automation

It reduced configuration creep instead of adding to it.

For me, the real challenge in 2026 isn’t features — it’s balancing flexibility with consistency without over-engineering Jira.

Curious what’s breaking first for others right now?

[Sara Chieco]

The insane buggy-ness of the current experience is mind boggling. between switching work list criteria on the fly to some other random project that exposes tickets to the wrong client, to cards just not opening, or randomly closing, it's infuriating to be paying for this at this point.

The last release destroyed our use of JIRA. It's been months and we STILL cannot use the system in remotely the efficient way we used to. Other platforms have been suggested that we are evaluating because the cramped ridiculous left nav (which I might remind them they tried another time years ago and promptly moved back to top nav) is the worst UX change I might have ever experienced. 

Atlassian shows zero interest in having a competent UX team, and I don't see that changing.

[Shanmuga Narayanan Pitchaipillai]

Change Fatigue and Reliability woes. 

Too many changes and incoherent change implementation . 

Everytime i have to ask my team to learn the navigation and terminologies that is not necessarily a primary value creator , it becomes a major challenge 

[Luke Gackle]

I totally agree with OPs viewpoint, but I am going to have to go with: 3) Automation: powerful, but not always flexible

The drift in support for JIRA Integrations is shocking, Atlassian implemented a 365 day expiry on API keys which is a sensible security move, and implemented a new service account feature with Oauth support so they don't expire, Brilliant! Except that no one wants to take ownership of updating and maintaining the Jira integration in Microsoft Power Automate, this integration does NOT support service accounts via Oauth, it only supports user accounts via Oauth.

So now I am having to create my own custom workflows to integrate with the Jira API so that I can actually create a reliable workflow process that won't fall over when I leave the organisation (because ya'know API keys are user based).

This all comes down to bad architecture and lack of foresight around what these changes really mean for customers.

I could list a hundred other things that annoy me about the Atlassian platforms but we'll leave it there for now 😅

[Arkadiusz Wroblewski]

@Luke Gackle Definitely Agree. For basics ? Sure, but complicated things - No other choice than Scriptrunner or API.

[Becker_ Rene]

For me the biggest challenge is the frequent feature updates. The other topics I can handle and are working for me (not always, but we negotiate).

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The feature request are really difficult for me thouth. Atlassian keeps breaking stuff, rolling out without checking impacts and do undereliver constantly ... and making me the one that has to advocate for it.

What annoys me the most, is that - basically always -, Atlassian looks at their new implementations like every customer only had ~100 users. They change something and provide neither API or central management to change any behaviour Atlassian thought best. Which means everything must be dealt with manually.

Or adding Rovo as a default app to all instances. OK, I am halfway thankful for that. But higher entity forbid, you have to remove Shadow-IT instances. Then you learn how again this was implemented only half the way.

The second most annoying thing is, Atlassian adding features and advocating for them like they just invented a immortatlity-serum. And then it's stuff like Confluence databases which has an implementation looking like an iframe, no possibility to use it in diagram macros etc. So basically it's like a table with more ... no ... less options. I hate when they do that and I fall for it everytime. (hope never dies). I still remember the 1hr+ presentation and all the "excitement" of the host, while I was like "ok ... and what now? Give me a use case".

The relevant updates, though (like: hey, we are going to break all your Jira Boards) are not announced or are sometimes sold as a new feature (in this case bringing back an old one) but leaving out that they are going to mess up the implementation.

Don't get me wrong ... there are good changes too (like Confluence Folders). But they have become the exception. 

The worst thing about it? We are paying a s*it load of money and the product keeps degrated with every update.

Honestly ... I wished we could roll back to the old server version. At least we were able to fix every screw up by scripting and modification. Now we just have to live with them and pray that they don't break anything this time.

And yes ... we are discussing whether it has become viable to move to a more stable platform (not Microsoft though) 

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