Outline/number formatting behavior

I can't get Outline format to lock in.  When I set it I get the first letter, but when it hit return and get the second letter; and hit Tab, a space is entered in the line but the letter doesn't change to a number and indent; like it should.

Also the numbering icon keeps lighting up.  I've attached the word document that I was trying to create an Outline in and have failed completely.

This is not rocket science, I have never seen this kind of behavior before.

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Paul SauvéConnect With a Mentor RetiredCommented:
What I usually do is open the document and use the Outline view: View -> Outline.

Then you can use the arrows to select the required Level, each Level corresponds to a Heading paragraph style and Body Text corresponds to Normal style:
Level 1 = Heading 1 paragraph style, etc.
No matter what the level, when you hit Enter, the following paragraph style is Normal, by default.Outline View
rfportillaConnect With a Mentor Commented:
This would be funny if not so frustrating.  

The problem is in how Word handles the Headings.  When you hit enter, you go into typing content (not a heading).  Therefore, formatting is reset to standard normal.  

When you switch into numbering (or outline), Word looks to continue a previous list and restores those formats.

Workaround 1: Don't use numbering or outlines for headers.  You can still use the Roman numberals, but unset the numbering format (just click it off).  As you type, if you click undo or ctrl+z it will undo the immediate, last autoformat.

Workaround 2: Use the numbering dropdown instead of the button.  It's the little arrow right next to the button.  This seems to work for whatever reason.

Good luck.  Let me know if you have any issues.
mikecox_Author Commented:
Ok, let me sort these and see if I can makes sense of it.

What baffles me is why this option is virtually impossible to use.  It used to work, I used to use the Outline option all the time; when did it become useless and why hasn't it been fixed?  It works in other programs; like Evernote.
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As mentioned above, this is a quirk related to using the header.  A header is typically only one line so when you hit enter, it knows to reset the formatting to normal.  Numbering looks for existing numbering lists in the document and restores that formatting (which in this case, is also the header format).  This is an odd case where they work against each other.  

I posted 2 options above.  Take a look and let me know if you are still having an issue.
I don't think Evernote has embedded bookmarks in it that allow you to set up dynamic document outlines, indexes and TOC's like Word.  Unfortunately, there were trade-offs made here for the extra functionality.
mikecox_Author Commented:
Evernote creates perfect outline format; I don't know about dynamic document outline or indexes or TOC's, I just know I can create an outlined document with ease.  At one time, a very long time ago, I was able to do the same thing in Word; now it is impossible, without jumping though hoops that complicate the process.   How do serious professional; like legal secretaries manage to get any work done?  Clearly the Outline option doesn't work and the icon misleads the user into thinking it will.

I don't like these options at all; it's not your fault, it's MS's fault.  I will move to Evernote to work on my Outline; it's seamless, and it work perfectly.
mikecox_Author Commented:
It's not really an Excellent solution because the excellent solution would be for MS to make the Outline option work; like it's supposed to.  

Paul's option turned out to work best for me.
Paul SauvéRetiredCommented:
I think the easiest thing to do is create the outline in plain text and use the Outline View afterwards to set up the proper levels... Or simply use the Heading 1, Heading 2, Heading 3, etc. paragraph styles as you write your document.
mikecox_Author Commented:
Yes, I'm afraid your right!  I just don't understand why there isn't a huge outcry over this or why MS allows this to go unfixed.
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