A customer asked today if he could pay for a shipping upgrade, which is odd because I have my shipping profile set for free regular shipping with an upgrade to Priority option. I’ve had it this way for years. I opened an incognito browser to see what a customer sees and there is no option for choosing the upgrade. So, is something missing from my settings, or is Etsy just glitching?
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Please double check your setting under Shipping Settings Rates & upgrades.
Click on Settings > Shipping Settings > Rate and upgrades > then click on Enable underneath Shipping Upgrades.
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Thanks for the suggestion; yes, I have upgrades enabled.
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Are they possibly an international customer?
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Nope, from Oregon.
Ok, I think I may have figured it out. I had the “free shipping guarantee” turned on. So anything over $35 ships for free. I disabled that, and now I can see the upgrade option in the cart. So looks like if you have a total of $35 that it overrides the shipping profiles?? I have free shipping on everything anyway, so I’ll keep that “guarantee” off.
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Ok, nevermind. I turned the guarantee back on and I see the same thing now. Maybe it was just a temporary glitch, but both my customer and I couldn’t see the upgrade option earlier. 
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