So far we've only seen random instances of the bug occurring and haven't been able to reliably reproduce it with identifiable parameters. For the time being, we can only hypothesise that the bug is caused by an incomplete loading/rendering of the forum's posting/editing interface.
Posting images is a basic function, but besides linking to an external site (whereby the [img] code is used), the "insert image" button also allows users to upload images as attachments. This is a function that requires the forum system to check permissions and ascertain whether the user using that function has sufficient permissions to upload attachments. An incomplete loading/rendering of the posting interface may cause discrepancies between the verdict handed down by the server ("user is allowed/not allowed to do this function") and your browser receiving it ("I have/don't have permission").
This may cripple the permission checking procedure. The system errs on the side of caution, so if confirmation ("yes, I've received the permit, I'm going to proceed with what I was going to do") isn't explicitly obtained from a user who was asking for permission, it's going to assume that the user isn't permitted to do the function she wanted to execute. This could be the reason behind the button being greyed out, as if you didn't have permission to post images, and why it only happens intermittently.
As a side note, while connection lags can be caused by a myriad of things, browsing the forum with a VPN may increase the possibility of this happening. The increase in latency, even though hardly noticeable, may just be enough to trigger this minor annoyance every now and then. From our side, we've cleared the CDN cache just now. Short of the code itself being faulty, for the time being, this is the best explanation we can come up with.