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How do I upload pictures onto the showcase?

By "showcase", are you refering to the Painting & Modeling Showcase sub-forum, or do you mean the Dakka Gallery?

The Showcase forum works like any other part of the forum. You can attach/upload images directly to a post by using the "attachments" button just underneath the main text field for your post, or you can link to them using the [img ] tags if the pictures are already posted in our Gallery or elsewhere on the web. Remember that the figs need to be completely finished and based, and you need to include at least one pic in the first post when you make a thread. And remember not to attach anything to Dakka that includes profanity or isn't directly related to wargaming.

If you want to upload pics to the Gallery, the process is pretty darn simple. Go here:
http://www.dakkadakka.com/core/gallery-upload.jsp

Remember not to upload anything with profanity or anything not related to wargaming.

Also, you cannot use Flickr, apparently....

_Tim?

We've found that some free picture hosting sites either block external hotlinking entirely, or limit it and shut it down once you have more than a certain number of pageviews and it starts costing them more bandwidth than they want to be drawn off to an external site where no one's looking at their advertising.