MS Word Outline Formatting Issue

Verify the settings for indentation around the "invisible" numbered items. Click in the first level 1 paragraph and then display the Multilevel List dialog box via Home > Multilevel List > Define New Multilevel List. (If you set up your list using a list style there are other available routes to get to the Multilevel List dialog.)

For more on the settings in the dialog box, see https://shaunakelly.com/word/numbering/numbering20072010.html .

Post back if you need further assistance—or just to tell us how it goes. :-)

In a multilevel list that uses Heading styles, whether a new Roman numeral appears when Enter is pressed depends on the style’s “Style for following paragraph” setting and on list/indent behavior.

To restore correct Roman numeral continuation:

1. Check the Heading style’s “Style for following paragraph”
   1. In Word, on the Home tab, right‑click the Heading style that is linked to the Roman numeral level (for example, Heading 1) and choose Modify.
   2. In the Modify Style dialog, set “Style for following paragraph” (or similar wording) to the same Heading style (for example, Heading 1 instead of Normal).
   3. Select OK.
   With this setting, pressing Enter at the end of a numbered heading creates another paragraph in the same numbered Heading style, so the next Roman numeral appears automatically.
2. Ensure the multilevel list is correctly defined and attached to Heading styles
   1. Place the cursor in a correctly numbered paragraph at the Roman numeral level.
   2. On the Home tab, in the Paragraph group, click the arrow next to Multilevel List and choose Define New Multilevel List.
   3. Confirm that the appropriate list level is linked to the correct Heading style and that the number style is set to Roman numerals.
   4. Select OK.
3. If using Tab/Shift+Tab to change levels, make sure list tab behavior is enabled
   1. Go to File > Options > Proofing.
   2. Click AutoCorrect Options.
   3. On the AutoFormat As You Type tab, ensure the option that controls list indenting with tabs/backspace (for example, “Set left and first-indent with tabs and backspaces”) is checked, so Tab and Shift+Tab can promote/demote list levels.
4. If Track Changes is on, accept changes and turn it off for testing
   1. Accept all tracked changes in the document.
   2. Turn off Track Changes (Ctrl+Shift+E).
   3. Test pressing Enter at the end of a Roman‑numeral paragraph to see if the next numeral appears.

If the Heading style’s “Style for following paragraph” is set to Normal or another non‑numbered style, pressing Enter will create an unnumbered paragraph instead of continuing the Roman numerals. Setting it to the same Heading level restores automatic numbering.

References:

• Having headings in multilevel list disables automatic numbering - Microsoft Q&A
• Define new bullets, numbers, and multilevel lists
• How do you restore using tab to change outline/bullet levels? - Microsoft Q&A
• Use a screen reader to track and review changes in a document in Word