diff --git a/modules/caddyhttp/reverseproxy/httptransport.go b/modules/caddyhttp/reverseproxy/httptransport.go
index 8d06d3bd274..db806acbd3f 100644
--- a/modules/caddyhttp/reverseproxy/httptransport.go
+++ b/modules/caddyhttp/reverseproxy/httptransport.go
@@ -412,8 +412,13 @@ func (h *HTTPTransport) NewTransport(caddyCtx caddy.Context) (*http.Transport, e
 			return nil, fmt.Errorf("making TLS client config: %v", err)
 		}
 
-		// servername has a placeholder, so we need to replace it
-		if strings.Contains(h.TLS.ServerName, "{") {
+		serverNameHasPlaceholder := strings.Contains(h.TLS.ServerName, "{")
+
+		// We need to use custom DialTLSContext if:
+		// 1. ServerName has a placeholder that needs to be replaced at request-time, OR
+		// 2. ProxyProtocol is enabled, because req.URL.Host is modified to include
+		//    client address info with "->" separator which breaks Go's address parsing
+		if serverNameHasPlaceholder || h.ProxyProtocol != "" {
 			rt.DialTLSContext = func(ctx context.Context, network, addr string) (net.Conn, error) {
 				// reuses the dialer from above to establish a plaintext connection
 				conn, err := dialContext(ctx, network, addr)
@@ -422,9 +427,11 @@ func (h *HTTPTransport) NewTransport(caddyCtx caddy.Context) (*http.Transport, e
 				}
 
 				// but add our own handshake logic
-				repl := ctx.Value(caddy.ReplacerCtxKey).(*caddy.Replacer)
 				tlsConfig := rt.TLSClientConfig.Clone()
-				tlsConfig.ServerName = repl.ReplaceAll(tlsConfig.ServerName, "")
+				if serverNameHasPlaceholder {
+					repl := ctx.Value(caddy.ReplacerCtxKey).(*caddy.Replacer)
+					tlsConfig.ServerName = repl.ReplaceAll(tlsConfig.ServerName, "")
+				}
 
 				// h1 only
 				if caddyhttp.GetVar(ctx, tlsH1OnlyVarKey) == true {
diff --git a/modules/caddyhttp/reverseproxy/httptransport_test.go b/modules/caddyhttp/reverseproxy/httptransport_test.go
index 1fa4965f251..88ac9d5916d 100644
--- a/modules/caddyhttp/reverseproxy/httptransport_test.go
+++ b/modules/caddyhttp/reverseproxy/httptransport_test.go
@@ -1,11 +1,13 @@
 package reverseproxy
 
 import (
+	"context"
 	"encoding/json"
 	"fmt"
 	"reflect"
 	"testing"
 
+	"github.com/caddyserver/caddy/v2"
 	"github.com/caddyserver/caddy/v2/caddyconfig/caddyfile"
 )
 
@@ -115,3 +117,81 @@ func TestHTTPTransport_RequestHeaderOps_TLS(t *testing.T) {
 		t.Fatalf("unexpected Host value; want placeholder, got: %s", got)
 	}
 }
+
+// TestHTTPTransport_DialTLSContext_ProxyProtocol verifies that when TLS and
+// ProxyProtocol are both enabled, DialTLSContext is set. This is critical because
+// ProxyProtocol modifies req.URL.Host to include client info with "->" separator
+// (e.g., "[2001:db8::1]:12345->127.0.0.1:443"), which breaks Go's address parsing.
+// Without a custom DialTLSContext, Go's HTTP library would fail with
+// "too many colons in address" when trying to parse the mangled host.
+func TestHTTPTransport_DialTLSContext_ProxyProtocol(t *testing.T) {
+	ctx, cancel := caddy.NewContext(caddy.Context{Context: context.Background()})
+	defer cancel()
+
+	tests := []struct {
+		name                    string
+		tls                     *TLSConfig
+		proxyProtocol           string
+		serverNameHasPlaceholder bool
+		expectDialTLSContext    bool
+	}{
+		{
+			name:                 "no TLS, no proxy protocol",
+			tls:                  nil,
+			proxyProtocol:        "",
+			expectDialTLSContext: false,
+		},
+		{
+			name:                 "TLS without proxy protocol",
+			tls:                  &TLSConfig{},
+			proxyProtocol:        "",
+			expectDialTLSContext: false,
+		},
+		{
+			name:                 "TLS with proxy protocol v1",
+			tls:                  &TLSConfig{},
+			proxyProtocol:        "v1",
+			expectDialTLSContext: true,
+		},
+		{
+			name:                 "TLS with proxy protocol v2",
+			tls:                  &TLSConfig{},
+			proxyProtocol:        "v2",
+			expectDialTLSContext: true,
+		},
+		{
+			name:                     "TLS with placeholder ServerName",
+			tls:                      &TLSConfig{ServerName: "{http.request.host}"},
+			proxyProtocol:            "",
+			serverNameHasPlaceholder: true,
+			expectDialTLSContext:     true,
+		},
+		{
+			name:                     "TLS with placeholder ServerName and proxy protocol",
+			tls:                      &TLSConfig{ServerName: "{http.request.host}"},
+			proxyProtocol:            "v2",
+			serverNameHasPlaceholder: true,
+			expectDialTLSContext:     true,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			ht := &HTTPTransport{
+				TLS:           tt.tls,
+				ProxyProtocol: tt.proxyProtocol,
+			}
+
+			rt, err := ht.NewTransport(ctx)
+			if err != nil {
+				t.Fatalf("NewTransport() error = %v", err)
+			}
+
+			hasDialTLSContext := rt.DialTLSContext != nil
+			if hasDialTLSContext != tt.expectDialTLSContext {
+				t.Errorf("DialTLSContext set = %v, want %v", hasDialTLSContext, tt.expectDialTLSContext)
+			}
+		})
+	}
+}
+