IIS 10 - HTTP to HTTPS redirect then route to Server Farm (ARR)

But I get the dreaded ERR_TOO_MANY_REDIRECTS error. I've tried moving the rewrite rule from web.config to the applicationHost.conf ... ServerFaultisaquestionandanswersiteforsystemandnetworkadministrators.Itonlytakesaminutetosignup. Signuptojointhiscommunity Anybodycanaskaquestion Anybodycananswer Thebestanswersarevotedupandrisetothetop Home Public Questions Tags Users Unanswered FindaJob Jobs Companies Teams StackOverflowforTeams –Collaborateandshareknowledgewithaprivategroup. CreateafreeTeam WhatisTeams? Teams CreatefreeTeam Teams Q&Aforwork Connectandshareknowledgewithinasinglelocationthatisstructuredandeasytosearch. Learnmore IIS10-HTTPtoHTTPSredirectthenroutetoServerFarm(ARR)-toomanyredirects AskQuestion Asked 1year,4monthsago Active 8monthsago Viewed 2ktimes 0 Ihadaurlrewriteruleintheweb.configofoneofthesitesonourserver.Butweareimplementingaserverfarmwithsitesonthesamephysicalservertoenable"hotswap"deployments,asoutlinedhere. Ifoundthislink,whichseemslikeitshouldworkasitisredirectingfirst,soitshouldn'thitthere-writerule...thenastherequestcomesbackasanHTTPSrequestsothefirstrulewouldbebypassed,thefarmrewriteshouldgetexecute.ButIgetthedreadedERR_TOO_MANY_REDIRECTSerror. I'vetriedmovingtherewriterulefromweb.configtotheapplicationHost.conf,sameerror. WhatamImissing? Secondaryquestion:Wouldtheweb.configtakeprecedencetotheapplicationHost.configrules? Web.congifrewriterule: applicationHost.configrewriterule: Thenmovedtheweb.configruletoapplicationHost.config SiteBindingRules: Farmbindings: iisrewritearriis-10 Share Improvethisquestion Follow editedJul14'20at23:59 crichavin askedJul14'20at23:36 crichavincrichavin 11144bronzebadges 4 Firstcheckifyourrewriterulesleadtotheredirectionloop,docs.microsoft.com/en-us/iis/extensions/url-rewrite-module/…andthencheckthewebapps(someappscanredirectinternallybacktoHTTP). – LexLi Jul15'20at0:24 @LexLithanks.Ourappwouldn'tinternallyroutebacktoHTTP,butI'mintheprocessofimplementingthetracing.ButIalsowaswonderingiftheARRtotheServerFarmwouldtriggertheSSLredirectasitisroutingtonotetheurlinthisishttp,nothttps.Icouldn'treallyfindanythingoutaboutthatandtriedchangingittohttps,butgota502errorwhenIdid. – crichavin Jul15'20at0:56 @LexLiIaddedfailedrequesttracing,butreallycan'tdeterminewhatitissaying.Thelastlineis:BytesSent="477",BytesReceived="612",HttpStatus="301",HttpSubStatus="0"isthe301aproblem? – crichavin Jul15'20at2:50 Hints:1)Usebrowser'sdevelopertoolstoanalyzehowmanyredirectionresponsesitreceives(thatleadstotheerror).2)ReviewFRTlogstoconfirmeachoftheresponses.3)LearnfromFRTlogswhoissuedeachoftheresponses(URLRewritemodule,oryourwebapp,orsomethingelse).Thatusuallyrevealstheculprit. – LexLi Jul15'20at3:36 Addacomment  |  0 Active Oldest Votes Knowsomeonewhocananswer?Sharealinktothisquestionviaemail,Twitter,orFacebook. 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