Creating a token by dragging a character sheet onto the map creates a token not associated with that character sheet.

Steps to reproduce:
Create/join a campaign as GM.
Create a character sheet. This needs no template.
Associate a token image with that characters sheet.
Drag that character sheet onto the map.
Observe that no character sheet is associated with that token.

Did you save the sheet after associating the token with the sheet? Any action performed on the sheet has to be saved (scroll to the bottom for the buttons). Not saying you didn't but just asking to eliminate that possiblity.

Also, did you associate the Token with the character BEFORE adding it to the character? Wiki: https://wiki.roll20.net/Linking_Tokens_to_Journals

I don't think we are on the same page.
At the start, there is no token, but the character sheet has a token image.
The token is created by dragging the character sheet onto the map.
The newly created token is not associated with the character sheet used to create it. Specifically, The "Represents Character" attribute of the token is "NoneGeneric Token".

To answer your question yes/no:
The character sheet was saved, but there was no token at the time. So no token existed to be associated with the character sheet at that time.

When you say "token" do you mean there is an image in the "Avatar" field, or do you actually mean there is an image in the "Default Token (Optional)" field?

Adding an avatar image only will allow you to drag that image out onto the VTT. I wouldn't be surprised to learn that that image is not "represents" to the character you drag it from (and that might be considered a bug).

The way to get a Token that represents a Character when you drag that Character out of the Journal and onto the VTT is:
1) create a Token
2) set it's Represents to the Character you want it to represent.
3) Set it's bars, auras, name, vision to what you want it to have when you drag it out of the journal
4) Edit the Character
5) Add that token as the Default Token (optional)

From now on, when you drag the Character out of the Journal and onto the VTT, it will have the state you configured in steps 2 and 3.

I see. I had read the wiki link, but I didn't follow the internal mechanisms they were implying.
Wiki: https://wiki.roll20.net/Linking_Tokens_to_Journals

When you associate a token with the character sheet, it associates an instantaneous snapshot of the tokens stats. It does NOT actually associate the token with the character sheet. I thought it was just associating the token image with the character sheet, since when I pulled out a new token, it was always identical to the default token template, which was the token's status when I associated the token to the character sheet.

I would still call this a bug, but you can close this as a "feature" if you want, since it is well known and documented. The current methodology does enable the quick creation of identical mobs, but you could handle that better by having a "unique" checkbox on the character settings that has created token's "bar" stats unlinked.

My previous 2 posts were typed before I saw The Aaron's immediately preceding posts, as they were posted as I was typing up my posts and the posts are not auto-updated.

For clairification:
Token -> the token on the VTT
character sheet -> journal entry
I was erroneously referring to the token image as the character sheets "default token" which stored an outdated copy of the token.
I was never refering to the avatar.