diff --git a/queue/direct.go b/queue/direct.go
index 6072fd6..1129b2e 100644
--- a/queue/direct.go
+++ b/queue/direct.go
@@ -728,7 +728,13 @@ func deliverHost(log mlog.Log, resolver dns.Resolver, dialer smtpclient.Dialer,
 			rcpts[i] = mr.msg.Recipient().XString(m0.SMTPUTF8)
 		}
 
-		resps, err := sc.DeliverMultiple(ctx, mailFrom, rcpts, size, msg, has8bit, smtputf8, m0.RequireTLS != nil && *m0.RequireTLS)
+		// Only require that remote announces 8bitmime extension when in pedantic mode. All
+		// relevant systems nowadays should accept "8-bit" messages, some unfortunately
+		// don't announce support. In theory we could rewrite the submitted message to be
+		// 7-bit-only, but the trouble likely isn't worth it.
+		req8bit := has8bit && mox.Pedantic
+
+		resps, err := sc.DeliverMultiple(ctx, mailFrom, rcpts, size, msg, req8bit, smtputf8, m0.RequireTLS != nil && *m0.RequireTLS)
 		if err != nil && (len(resps) == 0 && n == len(msgResps) || len(resps) == len(msgResps)) {
 			// If error and it applies to all recipients, return a single error.
 			return deliverResult{err: inspectError(err)}
diff --git a/smtpclient/client.go b/smtpclient/client.go
index ee7380b..04e4524 100644
--- a/smtpclient/client.go
+++ b/smtpclient/client.go
@@ -1095,8 +1095,8 @@ func (c *Client) TLSConnectionState() *tls.ConnectionState {
 // mailFrom must be an email address, or empty in case of a DSN. rcptTo must be
 // an email address.
 //
-// If the message contains bytes with the high bit set, req8bitmime must be true. If
-// set, the remote server must support the 8BITMIME extension or delivery will
+// If the message contains bytes with the high bit set, req8bitmime should be true.
+// If set, the remote server must support the 8BITMIME extension or delivery will
 // fail.
 //
 // If the message is internationalized, e.g. when headers contain non-ASCII
@@ -1149,10 +1149,7 @@ func (c *Client) DeliverMultiple(ctx context.Context, mailFrom string, rcptTo []
 	}
 
 	if !c.ext8bitmime && req8bitmime {
-		// Temporary error, e.g. OpenBSD spamd does not announce 8bitmime support, but once
-		// you get through, the mail server behind it probably does. Just needs a few
-		// retries.
-		c.xerrorf(false, 0, "", "", nil, "%w", Err8bitmimeUnsupported)
+		c.xerrorf(true, 0, "", "", nil, "%w", Err8bitmimeUnsupported)
 	}
 	if !c.extSMTPUTF8 && reqSMTPUTF8 {
 		// ../rfc/6531:313