The American Men’s Internet Survey (AMIS) is conducted annually with 10,000 men age 15 + who have sex with men (MSM). Modeling was used with 39,863 AMIS surveys from 4 cycles between December 2013 to February 2017 to identify temporal trends in sexual behavior, substance use, and testing behavior (within 12 months preceding interview) stratified by participants’ self-reported HIV status. HIV-negative/unknown status MSM had significant increases in condomless anal intercourse (CAI), marijuana use, use of other illicit substances, sexually transmitted infection (STI) diagnoses, and HIV or STI testing (testing only increased among MSM age 25 +). HIV-negative/unknown status MSM had significant decrease in CAI with an HIV-positive or unknown status partner. HIV-positive MSM had significant increases in CAI, methamphetamine use, and STI diagnoses/testing. Although encouraging, the few indicators of improvement in HIV/STI sexual health practices are not consistently seen across sub-groups of MSM and may be counteracted by growing proportions of MSM engaging in CAI and acquiring STIs.