If the first action in a new document is modifications to styles, then toolbar's UNDO button is not activated (until another kind of edit is made).
Steps to reproduce:
1. Create a new Writer document
2. As the first edit, modify styles:
2.1. Page style: menu Format->Page->Page tab->Orientation->toggle Landscape->OK (this modifies "Default Style", and makes immediate visible on-screen result).
2.2. List style: Sidebar->Styles and Formatting->List Styles->right-click Numbering 1->Modify...->Options->Number->A, B, C, ...->OK.
2.3. Frame style: Sidebar->Styles and Formatting->Frame Styles->right-click Frame->Modify...->Wrap->Spacing->modify a spacing->OK.
2.4. Character style: Sidebar->Styles and Formatting->Character Styles->right-click Numbering Symbols (because Default style is not editable)->Modify...->Font->select another font->OK.
2.5. Paragraph style: Sidebar->Styles and Formatting->Paragraph Styles->right-click any currently unselected style (in my case, Default Style is selected, so I tested Caption)->Modify...->Font->select another font->OK.
Expected result: after any of these actions, UNDO toolbar button should be activated.
Actual result: UNDO button stays inactive.
The menu Edit->Undo is, however, properly activated, and Ctrl+Z works properly regardless of the toolbar button state. Also, making edits to document, as well as modifying active paragraph style, activates the button, and all the previous style edits are then listed in the button's drop-down list.
It is of a very low impact, as easy workarounds are available, and the problem doesn't prevent any work.
Tested with: Version: 188.8.131.52
Build ID: c4c7d32d0d49397cad38d62472b0bc8acff48dd6
Reproducible with LO 184.108.40.206, Win 8.1
Same thing reproduced on Linux / LO 220.127.116.11, so not a regression
(equally on current master, but there the menu item is also disabled - although a keyboard Ctrl+Z still works)
-> Version: Inherited from OOo
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*** This bug has been marked as a duplicate of bug 47807 ***