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When integrating custom payment gateway to CiviCRM/Wordpress what is the best approach to use so that when you update CiviCRM to newer versions your payment gateway integration files will not be affected?

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Put your code in a native CiviCRM Extension! There are a number of Payment Processor Extensions already available - go here:

https://civicrm.org/extensions/home?title=&body_value=payment&field_extension_cms_tid=All&field_extension_ready_value=All&sort_by=title&sort_order=DESC

That will find most of them!

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