Upload multiple custom packages to a software title on one team

[eugkuo]

Goal

User story
As an IT admin,
I want to host multiple software installers under one software title
so that I can manage installers for different architectures in one place.

Key result

Customer reequest

Original requests

• Upload multiple custom packages for a software title on one team #25407

Context

• Design: @eugkuo
• Dev: @mostlikelee

Changes

Product

• UI changes:
  • Figma design file
  • Prototype
• CLI (fleetctl) usage changes: TODO
• YAML changes: TODO
• REST API changes: TODO
• Fleet's agent (fleetd) changes: TODO
• GitOps mode changes: TODO
• Activity changes: TODO
• Permissions changes: TODO
• Changes to paid features or tiers: TODO
• My device and fleetdm.com/better changes: TODO
• First draft of test plan added
• Other reference documentation changes: TODO
• Once shipped, requester has been notified
• Once shipped, dogfooding issue has been filed

Engineering

• Test plan is finalized
• Contributor API changes: TODO
• Feature guide changes: TODO
• Database schema migrations: TODO
• Load testing: TODO

ℹ️  Please read this issue carefully and understand it. Pay special attention to UI wireframes, especially "dev notes".

QA

Risk assessment

• Requires load testing: TODO
• Risk level: Low / High TODO
• Risk description: TODO

Test plan

Make sure to go through the list and consider all events that might be related to this story, so we catch edge cases earlier.

1. Step 1
2. Step 2
3. Step 3

Testing notes

Confirmation

1. Engineer: Added comment to user story confirming successful completion of test plan.
2. QA: Added comment to user story confirming successful completion of test plan.

[eugkuo]

@mostlikelee I've added a Prototype that I think captures and expands upon our conversation yesterday.

I've added this to DR today to discuss, but if you get a chance lmk what you think.

cc @noahtalerman

[eugkuo]

Questions from 15 April 2025 design review.

1. How restrictive do we want to be? Can people upload installers for the same version. Can have MSI and exe installer for the same version. Are we going to allow them to do that?
   1. @mostlikelee to think about this a little more. :-)
2. What do we do if someone tries to upload an installer that does not match with the software title?
   1. @eugkuo would rather fail these so that people don't end up with 1Password and Brave attached to the Zoom software title
   2. @ksykulev Unf we can't always validated well
   3. @mostlikelee Maybe it's a warning rather than an error