Hi,
I think if you upload your snapshot through the SimBrief website (by selecting “Update - Upload a new weather snapshot”), it forces Active Sky to redownload historical weather before uploading to SimBrief. When it does this, it might be erasing your custom wind direction.
Instead, try setting your custom Active Sky winds, then right-clicking the SimBrief Downloader icon in the Windows taskbar (bottom right of your screen near the clock) and choosing “Upload Active Sky Weather”.
Once that’s done, go back to SimBrief and in the Historical Weather section, choose “Enabled - Use your uploaded snapshot”. If it warns you that your departure date does not match your snapshot, make sure to choose “Change Date”, and not “Upload Snapshot”.
Best regards,