diff --git a/src/net/http/omithttp2.go b/src/net/http/omithttp2.go
index 307d93a3b14b3c..7e2f4925798f81 100644
--- a/src/net/http/omithttp2.go
+++ b/src/net/http/omithttp2.go
@@ -32,7 +32,7 @@ type http2Transport struct {
 func (*http2Transport) RoundTrip(*Request) (*Response, error) { panic(noHTTP2) }
 func (*http2Transport) CloseIdleConnections()                 {}
 
-type http2erringRoundTripper struct{}
+type http2erringRoundTripper struct{ err error }
 
 func (http2erringRoundTripper) RoundTrip(*Request) (*Response, error) { panic(noHTTP2) }
 
diff --git a/src/net/http/transport.go b/src/net/http/transport.go
index d0bfdb412cb834..15feeaf41fd611 100644
--- a/src/net/http/transport.go
+++ b/src/net/http/transport.go
@@ -569,14 +569,11 @@ func (t *Transport) roundTrip(req *Request) (*Response, error) {
 		}
 
 		// Failed. Clean up and determine whether to retry.
-
-		_, isH2DialError := pconn.alt.(http2erringRoundTripper)
-		if http2isNoCachedConnError(err) || isH2DialError {
+		if http2isNoCachedConnError(err) {
 			if t.removeIdleConn(pconn) {
 				t.decConnsPerHost(pconn.cacheKey)
 			}
-		}
-		if !pconn.shouldRetryRequest(req, err) {
+		} else if !pconn.shouldRetryRequest(req, err) {
 			// Issue 16465: return underlying net.Conn.Read error from peek,
 			// as we've historically done.
 			if e, ok := err.(transportReadFromServerError); ok {
@@ -1637,7 +1634,12 @@ func (t *Transport) dialConn(ctx context.Context, cm connectMethod) (pconn *pers
 
 	if s := pconn.tlsState; s != nil && s.NegotiatedProtocolIsMutual && s.NegotiatedProtocol != "" {
 		if next, ok := t.TLSNextProto[s.NegotiatedProtocol]; ok {
-			return &persistConn{t: t, cacheKey: pconn.cacheKey, alt: next(cm.targetAddr, pconn.conn.(*tls.Conn))}, nil
+			alt := next(cm.targetAddr, pconn.conn.(*tls.Conn))
+			if e, ok := alt.(http2erringRoundTripper); ok {
+				// pconn.conn was closed by next (http2configureTransport.upgradeFn).
+				return nil, e.err
+			}
+			return &persistConn{t: t, cacheKey: pconn.cacheKey, alt: alt}, nil
 		}
 	}