If using hivesigner, that can be problematic. If the image is not too large, i would sign in using Keychain and go through that browser. I havent done it with images but shorts had issues with hivesigner. When using Keychain, I found no problems.
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This is via the keychain browser. Must be the server as you mentioned since it works fine on PeakD using the exact same process.
The easiest way might be to post through inleo and edit through peakd to add the photo via your phone.
Just an idea.