Hi Rburge_esriau

I tried to use both
and br and i can confirm that they are not working on Textarea,however you can use Rich Text instate of Textarea e.g

1. Add a Rich Text control to a view or a form.
2. On your view or form layout, click on the Rich Text to access its properties.
3. Under General, click on the expression's ellipsis to add an expression.
4. Click on the Add button to configure the expression. On the Context Browser, open the Operations tab and expand the operation Text.
5. Drag an HTML Encode and then add the view's SmartObject properties from the Context tab.
6. Type in the expression <br> to break to a new line. 

Ref:https://help.k2.com/support-services/kbt148173

Regards

Elvis

Good day  @rburge_esriau ;

Have you also tried the trim text functionally on the context browser for expression (Removes leading and trailing spaces and line breaks from a string).

Referenced (https://help.k2.com/onlinehelp/k2cloud/userguide/current/default.htm#K2-Workflow-Designer/Use/ContextBrowser/Functions/Functions.htm).

Kind regards;

Widson.

Only way that we can do this just for record

- Load data into SharePoint Online as Multiple Line with line breaks.

- Add line break at end of record in SharePoint Online

- Call SmartObject down so you can use the content of the SharePoint field

This is not a solution by any stretch and should be something K2 are looking to improve in future release of Cloud UI. Text Areas are supposed to be multiple line options and creators are being limited by only being able to use single line rules for these fields.