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Unless the option for "Enable Alt-Click to send mail" is enabled, the option "Auto-Attach similar items on Control-Click" does not work.
WoW version: Retail, 8.2.5
Postal version: 3.60
This is by design. If you look at the express options menu when you disable the "Enable Alt-Click to send mail" the option for "Auto-Attach similar items on Control-Click" greys out to indicate this is not support when "Enable Alt-Click to send mail" is disabled.
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