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Current/Past Pricing (2020)
We will considerWe paid $17,500 in 2020 to renew Jira license. Jira's license expires in July 2021.
We paid $13,100 in 2020 to renew Confluence. Confluence's license expires in Feb 2021.
Both these prices were artificially low, as we are on an 'advantaged' (grandfathered) plan that escaped the 2019 price increases (non-grandfathered renewal costs were $30,000 and $22,500 for Jira and Confluence respectively).
Plugins are not considered here as their costs are dwarfed by the base costs, but increases moving to Cloud can be assumed (e.g. 20% for Tempo Timesheets, 600% for JETI).
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Our base spend (Jira + Confluence) will thus increase 10x or 11x from its current $30,600 
Recommendations
As an Atlassian product consultant I am very unimpressed with Atlassian's move. I have written up my (sanitized) thoughts on this move on my website. I have also put up a website for exploring alternatives products, for users for whom a 10-11x price increase is infeasible:
In that context, what would I recommend?
The least disruptive move would be to move to The least disruptive move would be to move to Data Center, assuming we can afford it (the 'DC, after Feb 1, 2021' column). Moving early will lock in some discounts. Just be aware that DC is an annual subscription, not a perpetual license like Server, and that DC won't last forever (see blog post Betting on Atlassian DataCenter?). As happened with Server, DC is likely to undergo constant price increases to 'squeeze' larger customers onto Cloud.
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Jira's natural renewal date would be Jul 4 May 06, 2021, and Confluence's would be Feb Aug 17, 2021.
But, but renewing early before the price increase, we can save a bit of money. This is "Option 3: Renew on server early and lock in your existing price".
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- Renew Jira till Jul 4, 2021, for $17$2,500600.
- Renew Confluence till Feb 2022, for $2,000.
- Renew plugins, for $13$2,100773.
2022
Confluence Jira will be due for renewal in Feb May 2022, and Jira Confluence in Jul, Aug 2022.
However! Atlassian plan to stop selling license upgrades after Feb 2, 2022 and we know expect we'll need an upgrade to 10,000 users exceed the 50-user tier in this year2022. If we wait till Jul 4, 2022 to upgrade Jira May or August we'll be stuck on the 200050-user license tier forever.
So once again we must jump in early:. Prior to Feb 2, 2022
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we must upgrade Jira
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and Confluence from 50 to 100 users.
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"How long can I lock in my current pricing" FAQ in the Billing & licensing questions section of the Future server pricing page, it should be possible will to renew for 24 months:
So both our Jira 10,000 user license and Confluence 2,000 user license will last 24 months, from Jan 2022 till Jan 2024.
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The costs in Jan 2022 would thus be:
- $50,400 for Jira (2 x the $31$25,100 200 annual price for the 2000-10,000 user tier)
- $30,200 for Confluence (2x the $15,100 annual price for the 502-2000 user tier)
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