Place the insertion point in the paragraph and choose Restart Numbering from the context menu or choose Type > Bulleted And Numbered Lists > Restart Numbering. In normal lists, this command assigns the number 1 (or letter A) to a paragraph and makes it the first paragraph in a list. In multi-level lists, this command assigns the first lower-level number to a nested paragraph.
One of the harder things to do in Adobe InDesign, surprisingly for a page layout tool, is to create multilevel or outline format numbered lists.  The right way to accomplish this, according to the folks at Adobe, is to create a Style for every level of the list you’d like to have! Here are Adobe’s instructions on how to do so (This content is taken directly from https://helpx.adobe.com/indesign/using/bullets-numbering.html#create_multi_level_lists):

I want to point out that if this document is a fixed set of standards but will be amended in later editions, then autonumbers will increment, which is a bad idea. In legal documents, numbers are usually static, and deletions are struck-through, not deleted, to preserve the original numbering, so that older and newer editions can be compared number-by-number. Inserted and appended content would need to be manually numbered. You may want to create the first edition with autonumbering, then convert the numbered list numbers to text, to avoid unwanted renumbering in future editions.

Each section within an InDesign document can be numbered differently. This allows you to use one type of numerals to consecutively number a document's preface or other introductory materials and another numeral system for the remainder of the document. You must first define your document's sections, and then you can add section markers or page markers to your master pages. Apply the master page to document pages to include the section and page numbers on the document pages.
You probably know about Word's mail merge feature, and you might even use it to print labels or other documents, where some of the information changes (such as form letters). You can use the same feature with Publisher. Although you might not think of Publisher as an Office app, it comes with several different versions of Office. In this article, I'll show you how to print sequentially numbered tickets using Publisher and Excel. This article provides instructions for Publisher 2007, 2010, and 2013.
Thanks very much for your prompt reply, which reassured me that I was on the right path. From having read various Help topics, I suspected that I'd have to use an Excel data source for the numbers. Fortunately, my knowledge of Excel was good enough to know about the drag and drop facility to create automatic sequential numbering, so the data source creation was easy. In the end, it was the mail merge (no surprises?) which proved a tad tricky, but I got there in the end. I've used MM many times and quite happily in Word documents, but for Publisher label format, it was of course a bit different. The important bit that I had to discover for myself was the significance of, after getting to the Print stage, going into Print options, to Publication & Paper Settings, and selecting Multiple Pages per Sheet (& in my case, also "Single-sided" cos my default of duplex printing had come up). But TA-DA!  All is fine now. Thanks very much again.
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If you’re producing any kind of numbered items in-house that are multiple-up on a sheet where you need to control all the variables to meet your production needs, the autonumbering feature through numbered lists is the way to go! Just step and repeat away & InDesign will do all the work. No need to fool with a seperate “numbers” file or deal with a data merged document. I think it’s by far the best option for basic numbering.
@Aaron: I am stuck exactly with the same problem. I am constructing a style guide document, and thus my content is mainly images, not text. Still I do need numbered chapters in multiple levels, but the automatic numbering seems to be almost impossible as my headings are in separate text boxes. I have tried linking heading text areas, section markers, numbered lists and whatnot, but I am about to revert back to manual numbering instead of battling with this and wasting time! It’s just so devastating, I believe that machines should do what they do best, instead of people keeping track of numbering chapters!
Tip  Follow the same steps (above) to create Request for Production or Request for Admissions. The only difference would be in Step 3, you would change the "rog" to "rpf" or "rfa". This will keep unique numbering schemes running in the same document. Therefore, you could have an Interrogatory No.1 as well as Request for Production No.1. Keep in mind that if you cut, copy or paste sequence codes, you'll need to select them and press F9 to update the field codes. They do not update automatically.
One of the last things we need to do is our Table of Contents. We did this earlier, where we had different page numbering. So, all we need to do now is, because we've redefined all our Styles, and we're doing it all proper now, if we go to 'Layout'-- I've got my cursor flashing in here, first of all go to 'Layout', let's go to 'Update Table of Contents', and I'm going to click 'OK'. There's some spaces left in the front of this when I was messing around with it before, yours should be fine. So it's updated to the correct numbers. One thing I also did was I went in and adjusted the font from Medium to Light because I just liked it. I did that in between tutorials.
You can define a section prefix to label section pages automatically. For example, if you specify A– for Section Prefix on page 16 of a document and include the section prefix, the page will appear in the table of contents or index as A–16. Text you type for a section marker appears when you choose Type > Insert Special Character > Markers > Section Marker.
You can use Microsoft Word to create complex documents. Books and other large documents occasionally require different page number formats in different sections of one document. For example, you can number the index pages with Roman numerals (for example, "i.", "ii.", "iii.") and the main document with Arabic numerals (for example, "1", "2", "3"). This article describes how to set up different page numbering formats.
You can control whether your next paragraph number continues the current sequence or starts again at 1 within that same right-click menu. If one of your numbers gets out of sequence, simply right-click and choose Continue Numbering. If you want to force the number back to the beginning (say, you’re switching from interrogatories to requests for production), choose Set Numbering Value (which will also give you the option of continuing the previous list).

My quick process involves setting up a row of plaques with a01, a02, a03, thru a09. Then copy the plaques to the clipboard. Run the REPLACE TEXT feature to replace "a" with "1". Move row down and paste clipboard back into page. Run REPLACE TEXT to replace "a" with "2". Repeat until I get all the numbers. It's faster than manually typing the numbers in but I know there's go to be someway of automating the process.
If the list you want is as simple as "1", "2", "3", you'll appreciate how easy it is to apply this type of numbering in legal documents. Simple numbered lists are different in Word 2000 than they were in Word 97. In Word 2000, the default for even the most basic list is multi-level. For example, if you number an item and press Enter and then press the TAB key, Word automatically formats this number as the second level in an outline numbered list format. Single and multi-level numbering are explained later in this chapter.
Running captions number figures, tables, and other items consecutively in a document. For example, the first figure caption starts with the words “Figure 1,” the second with “Figure 2,” and so on. To make sure that figures, tables, or similar items are numbered consecutively, define a list for the item, and then create a paragraph style that includes the list definition. You can also add descriptive words such as “Figure” or “Table” to the numbering scheme of the paragraph style. numbering using publisher
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