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Is it possible in AL exchange multiple magic items all at once, respecting the rules for each exchange, between the same 2 characters through the usage of 15 downtime days (and not necessarily 15 downtime days for each exchange)?

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It is 15 days per individual item exchanged.

While not explicitly indicated, this fact is implied by the following quote from the DDAL Player's Guide (emphasis mine):

Each party to the trade must spend 15 downtime days to trade the item ... on a one-for-one basis.

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  • \$\begingroup\$ Your emphasis is awkward for me. "The" is both singular and plural. If it said "an item" I would straight forward agree with you. \$\endgroup\$ – HellSaint May 19 '18 at 15:25
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    \$\begingroup\$ I meant to emphasize item (singular) as well. Whoops @HellSaint \$\endgroup\$ – David Coffron May 19 '18 at 15:30
  • \$\begingroup\$ Fair enough. Still, it's kinda confusing. I have always understood the 15 days as the time for the characters to encounter each other, pretty much, since if the characters are in the same game session they can just trade freely without using any downtime. AL doesn't need to make sense though haha. \$\endgroup\$ – HellSaint May 19 '18 at 20:52
  • \$\begingroup\$ @HellSaint if you want a narrative friendly explanation, the 15 days can include the time it takes to teach the other person how to use the item effectively (while not that satisfactory since a short rest does that for most items,, it is a little more reasonable) \$\endgroup\$ – David Coffron May 19 '18 at 21:11

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