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I also have issues, which appear to be since 5.5. Worked beautifully previously but now have a range of issues.
Simply using 2 areas – one for text and other for an image – 2/3 and 1/3

A few pages still show the image correctly but the majority of pages still have the correct layout but no image is showing and one page, which had two images, shows one image and not the other. ??

Images all in the media area, nothing changed and path is same for all.

I am very new to WordPress so wonder how to fix.

Any suggestions?

OK – all solved.
As a newbie I was expecting that under Media Library, I would be given buttons to upload etc. Reading the forums, I felt this to be true.

Luckily, after numerous reinstalls, I found an official wordpress demo and that too had the same problem. This led me to think that if it appears WP can’t get it right, then perhaps I am looking for wrong things.

Then I found the magic line in the manual that told me to upload media through write pages/posts. All solved for me!

A little illogical for me but now one happy bunny. Now I can add all those marvellous plug-ins again!

I too am having problems with 2.6.1 and no media buttons.
I am a newbie to WordPress and was going spare as I just couldn’t find a way to upload files and couldn’t find a plug in to do the job.

I have done a fresh install via Fantastico on another site – no plugins, no additional templates – straight install. Still no buttons.

Should I just give up?