assignee.property is not a valid smart value.
assignee.properties smart values refer to entity properties, discussed in exhaustive detail at https://developer.atlassian.com/cloud/jira/platform/jira-entity-properties/
Entity properties are best set via the REST API as you can do bulk updates and use it to load entity-relevant information from external systems.
In Automation, these are set with the "Set Entity Property" action which lets you set properties for a Issue, Project or User. You've asked about assignee.properties so I will only discuss user properties, which in Automation are documented at https://support.atlassian.com/jira-software-cloud/docs/smart-values-users/
Tip: You can specify user-type custom fields in the "Set Entity Property", just type in {{issue.<custom field name>}}. Automation will protest a bit but it accepts it and it works fine.
Here's it used in a rule:
Run this rule and the Manager user listed on the AUTOTASK-1 issue now has a permanent entity property of "phoneNumber: 555-555-5555" going forward on that site.
Tip: You can load user entity properties outside a REST API by creating task issues in an AUTOTASK Task Management project:
Then Run the rule. Just make sure you turn off the notification scheme for that project. Going forward, you'll be able to load that property from the user in automations. A nice way to store information on users, like job title, phone number, location, time zone, etc. Make sure to store the Manager's account ID, if you want to store the user's Manager. Eventually the Atlassian User Profile should be accessible via automation, but there are always going to be use cases.
I like entity properties because they offer variables that are accessible everywhere in a rule. The "create variable" action only makes variables available in a local context, ie. within an if/else block or a branch.
When I want to make a new SLA, assignee.property is an option what jira suggests.
I'm not sure that's what Christine meant, but I'm also not sure that your answer apply to this. Maybe it is, but it's "property", and not "properties".
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