diff --git a/modules/caddyhttp/reverseproxy/healthchecks.go b/modules/caddyhttp/reverseproxy/healthchecks.go
index a737f116e..21fa0dfbb 100644
--- a/modules/caddyhttp/reverseproxy/healthchecks.go
+++ b/modules/caddyhttp/reverseproxy/healthchecks.go
@@ -438,9 +438,7 @@ func (h *Handler) doActiveHealthCheck(dialInfo DialInfo, hostAddr string, networ
 	// may be expected by handlers of this request
 	ctx := h.ctx.Context
 	ctx = context.WithValue(ctx, caddy.ReplacerCtxKey, caddy.NewReplacer())
-	ctx = context.WithValue(ctx, caddyhttp.VarsCtxKey, map[string]any{
-		dialInfoVarKey: dialInfo,
-	})
+	ctx = context.WithValue(ctx, dialInfoCtxKey, dialInfo)
 	req, err := http.NewRequestWithContext(ctx, h.HealthChecks.Active.Method, u.String(), requestBody)
 	if err != nil {
 		return fmt.Errorf("making request: %v", err)
diff --git a/modules/caddyhttp/reverseproxy/hosts.go b/modules/caddyhttp/reverseproxy/hosts.go
index e58d6825f..5c56c29e4 100644
--- a/modules/caddyhttp/reverseproxy/hosts.go
+++ b/modules/caddyhttp/reverseproxy/hosts.go
@@ -24,7 +24,6 @@ import (
 	"time"
 
 	"github.com/caddyserver/caddy/v2"
-	"github.com/caddyserver/caddy/v2/modules/caddyhttp"
 )
 
 // UpstreamPool is a collection of upstreams.
@@ -297,7 +296,7 @@ func (di DialInfo) String() string {
 // GetDialInfo gets the upstream dialing info out of the context,
 // and returns true if there was a valid value; false otherwise.
 func GetDialInfo(ctx context.Context) (DialInfo, bool) {
-	dialInfo, ok := caddyhttp.GetVar(ctx, dialInfoVarKey).(DialInfo)
+	dialInfo, ok := ctx.Value(dialInfoCtxKey).(DialInfo)
 	return dialInfo, ok
 }
 
@@ -329,9 +328,9 @@ type dynamicHostEntry struct {
 	lastSeen time.Time
 }
 
-// dialInfoVarKey is the key used for the variable that holds
+// dialInfoCtxKey is the context key used for the variable that holds
 // the dial info for the upstream connection.
-const dialInfoVarKey = "reverse_proxy.dial_info"
+const dialInfoCtxKey caddy.CtxKey = "reverse_proxy.dial_info"
 
 // proxyProtocolInfoVarKey is the key used for the variable that holds
 // the proxy protocol info for the upstream connection.
diff --git a/modules/caddyhttp/reverseproxy/httptransport_test.go b/modules/caddyhttp/reverseproxy/httptransport_test.go
index f64b58468..f4b4bf30c 100644
--- a/modules/caddyhttp/reverseproxy/httptransport_test.go
+++ b/modules/caddyhttp/reverseproxy/httptransport_test.go
@@ -260,7 +260,7 @@ func TestHTTPTransport_DialContext_DialInfoOverride(t *testing.T) {
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {
 			dialCtx := context.WithValue(context.Background(), caddyhttp.VarsCtxKey, make(map[string]any))
-			caddyhttp.SetVar(dialCtx, dialInfoVarKey, DialInfo{
+			dialCtx = context.WithValue(dialCtx, dialInfoCtxKey, DialInfo{
 				Network: "tcp4",
 				Address: tt.dialInfo,
 			})
diff --git a/modules/caddyhttp/reverseproxy/reverseproxy.go b/modules/caddyhttp/reverseproxy/reverseproxy.go
index 81a1ef1eb..fac56d482 100644
--- a/modules/caddyhttp/reverseproxy/reverseproxy.go
+++ b/modules/caddyhttp/reverseproxy/reverseproxy.go
@@ -660,11 +660,6 @@ func (h *Handler) proxyLoopIteration(r *http.Request, origReq *http.Request, w h
 		)
 	}
 
-	// attach to the request information about how to dial the upstream;
-	// this is necessary because the information cannot be sufficiently
-	// or satisfactorily represented in a URL
-	caddyhttp.SetVar(r.Context(), dialInfoVarKey, dialInfo)
-
 	// set placeholders with information about this upstream
 	repl.Set("http.reverse_proxy.upstream.address", dialInfo.String())
 	repl.Set("http.reverse_proxy.upstream.hostport", dialInfo.Address)
@@ -1037,7 +1032,14 @@ func (h *Handler) reverseProxy(rw http.ResponseWriter, req *http.Request, origRe
 			return nil
 		},
 	}
-	req = req.WithContext(httptrace.WithClientTrace(req.Context(), trace))
+	// attach to the request information about how to dial the upstream;
+	// this is necessary because the information cannot be sufficiently
+	// or satisfactorily represented in a URL
+	// it's set before request is roundtripped to avoid a race condition when
+	// http.Transport reads a newer value to dial a new connection when that new
+	// value is updated by another reverse proxy handler, typically forward_auth.
+	ctx := context.WithValue(req.Context(), dialInfoCtxKey, di)
+	req = req.WithContext(httptrace.WithClientTrace(ctx, trace))
 
 	// do the round-trip
 	start := time.Now()