Though popular, the magazine faced a series of legal challenges relating to obscenity, particularly from the US Post Office, which repeatedly attempted to declare it nonmailable.

[2] Beginning around 1943, the magazine gradually relaxed this self-censorship policy, with photos increasingly including visible pubic hair and genitals (initially from a distance).

[4]The photographs in the same issues were described as a combination of "action pictures showing nudists in their camp activities, rowing, hitting volley balls, building fires, etc."

In 1946, postal inspectors began an investigation of those placing letters and pen-pal notices in the magazine, suspecting them of sending nude photographs through the mail.

[1] In New York City in 1951, several newsstand clerks were arrested for selling copies of Sunshine & Health and SUN Magazine, violating a state statute prohibiting the distribution of obscene materials.

In January 1955, Boone's Sunshine Book Company filed a complaint in US district court seeking an injunction to stop the Post Office's continued seizure of the magazine.

Judge James Robert Kirkland ruled against the magazine, writing that the "American people are a clothed race", and identifying certain particular photographs as objectionable, such as a side view of a nude man with "the corona of his penis ... clearly discernible".

A short per curiam decision in Sunshine Book Co. v. Summerfield was handed down on January 13, 1958, finding in favour of the publisher, citing the earlier case Roth v. United States.