Calendars are not accepted at most correctional facilities, and a personalized calendar with photos is likely to be rejected at the mail room regardless of how it is packaged or sent.
The reasons facilities restrict calendars vary, but the most common concerns are the binding, the thickness, and the potential for concealment of contraband within the pages or spine. Some facilities also have blanket restrictions on items that could be used to track dates or coordinate activity, though this varies by security level.
Before ordering or sending anything, call the specific facility and ask directly whether printed calendars are permitted and whether there are any approved formats. Policies differ enough from one facility to the next that confirming first is always worth the few minutes it takes.
If the facility does not allow calendars, photos of you sent through InmateAid are an alternative that will almost certainly be permitted. Your inmate can keep them in their cell, which accomplishes the same goal of having you present in their daily environment.
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