The deadline for calendar-year exempt organizations is Monday, May 15, 2023. Failing to file the required Form 990-series return or notice for three consecutive years can result in automatic loss of exemption, as per Internal Revenue Code Section 5033(j). However, organizations requiring additional time can request a 6-month automatic extension by submitting Form 8868, the application for Extension of Time to File an Exempt Organization Return. It's important to note that while an extension grants more time to file, it does not extend the deadline for paying taxes. The IRS encourages organizations to electronically file Form 8868 when requesting an extension.