Thank you for your question.
Basically, how ms word/libreOffice work, either you apply a title style 
from the one provided in the gallery or to modify the hierarchical level of 
the text so it will be added to the TOC.
My current understanding (i'm really new to TW), or at least a strong 
feeling is that one of the use cases TW fullfits is to help to keep things 
organized, creating tiddlers is a nice feature but keeping relationship 
between them is more important, and imho TOC is such a fundamental feature.
To answer your question, maybe playing with tags in two ways:
- This tiddler is an element of TOC tiddler
- This tiddler is a child of annother tiddler
Should do the trick maybe ?
I have tried http://tw5magick.tiddlyspot.com/ "Table of Content creation" 
but for some reason it does not work

Le mercredi 6 août 2014 11:44:04 UTC+2, Michele Zaffalon a écrit :
>
> If you add tiddlers in random places inside your TW5, how can the TOC know 
> where they should exactly appear?
>
>
> On Wed, Aug 6, 2014 at 10:09 AM, <[email protected] <javascript:>> wrote:
>
>> I've maybe miss explained.
>> I'm looking for a way to add tiddlers is such a way they will be 
>> automatically inserted into a TOC. For large scale editing/commonly 
>> modified content, it's not trivial to keep a static TOC.
>> Is such a thing possible with TW5 ?
>>
>> Thank you in advance.
>>
>>
>> Le lundi 4 août 2014 12:19:56 UTC+2, [email protected] a écrit :
>>>
>>> Dear all,
>>>
>>> First of all, i would like to thank all who made tw such a great tool.
>>>
>>> I'm a developper, with no background in Javascript area, have never used 
>>> TW before,  and looking for any documentation that will optimize my use of 
>>> tw (single user use case).
>>> The possibility of using mathjax just fulfits 50% of my requirements for 
>>> instance.
>>>
>>> I'd like to experience the use TW5 as :
>>>
>>> 1- A design document : e.g https://drive.google.com/previewtemplate?id=
>>> 1K8JKFPtEA08EutfHK3U_3wDDn2SWvJdpue0rmjiX4a0&mode=
>>> public&urp=https://www.google.fr/&pli=1&ddrp=1# 
>>>
>>>    - I would like to be able to create/update sections in such a way to 
>>>    have the Table Of Content updated automatically, what could be the best 
>>> way 
>>>    to achieve this ?
>>>    - I would like to be able to export the whole DD as a printable (e.g 
>>>    pdf), is this currently possible ?
>>>
>>> 2- I would like to use TW5 to manage all my game text/translation. I use 
>>> GNU_gettext, i manly need to track the translation status of each string
>>>
>>>    - What could be the workflow to adopt in this case ? creating 
>>>    tag/tiddlers that correspond to String/Locales ?
>>>
>>> Any links to TW5 tutorial are more than welcome.
>>> Thank you all in advance.
>>>
>>>  -- 
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