diff --git a/lib/http.c b/lib/http.c
index d952b90ceb..ef2bd8f963 100644
--- a/lib/http.c
+++ b/lib/http.c
@@ -2000,17 +2000,17 @@ static CURLcode http_set_aptr_host(struct Curl_easy *data)
 {
   struct connectdata *conn = data->conn;
   struct dynamically_allocated_data *aptr = &data->state.aptr;
-  const char *ptr;
+  const char *ptr = NULL;
 
   curlx_safefree(aptr->host);
 #ifndef CURL_DISABLE_COOKIES
   curlx_safefree(data->req.cookiehost);
 #endif
 
-  ptr = Curl_checkheaders(data, STRCONST("Host"));
-  if(ptr &&
-     (!data->state.this_is_a_follow ||
-      Curl_peer_equal(data->state.initial_origin, data->state.origin))) {
+  if(Curl_peer_equal(data->state.initial_origin, data->state.origin))
+    ptr = Curl_checkheaders(data, STRCONST("Host"));
+
+  if(ptr) {
 #ifndef CURL_DISABLE_COOKIES
     /* If we have a given custom Host: header, we extract the hostname in
        order to possibly use it for cookie reasons later on. We only allow the
@@ -2047,30 +2047,40 @@ static CURLcode http_set_aptr_host(struct Curl_easy *data)
 #endif
 
     if(!curl_strequal("Host:", ptr)) {
-      aptr->host = curl_maprintf("Host:%s\r\n", &ptr[5]);
+      aptr->host = curl_maprintf("Host:%s", &ptr[5]);
       if(!aptr->host)
         return CURLE_OUT_OF_MEMORY;
     }
   }
   else {
-    /* Use the hostname as present in the URL if it was IPv6. */
-    char *host = (data->state.origin->user_hostname[0] == '[') ?
-       data->state.origin->user_hostname : data->state.origin->hostname;
+    /* This is the  HTTP Host: header, so we want
+     * - for ipv6 origins: "[ipv6-address]" where the ipv6 address is
+     *  found in origin->hostname, stripped of zoneid/scopeid.
+     * - the (IDN converted) origin->hostname (DNS name or ipv4) otherwise.
+     * Note: zoneid/scopeid  only applies to local routing and has no
+     * meaning on the remote HTTP server (eg. would confuse it). */
+    bool ipv6 = (bool)data->state.origin->ipv6;
+    struct dynbuf tmp;
+    size_t hlen;
+    CURLcode result;
 
-    if(((conn->given->protocol & (CURLPROTO_HTTPS | CURLPROTO_WSS)) &&
-        (data->state.origin->port == PORT_HTTPS)) ||
-       ((conn->given->protocol & (CURLPROTO_HTTP | CURLPROTO_WS)) &&
-        (data->state.origin->port == PORT_HTTP)))
-      /* if(HTTPS on port 443) OR (HTTP on port 80) then do not include
-         the port number in the host string */
-      aptr->host = curl_maprintf("Host: %s\r\n", host);
-    else
-      aptr->host = curl_maprintf("Host: %s:%d\r\n",
-                                 host, data->state.origin->port);
+    curlx_dyn_init(&tmp, DYN_HTTP_REQUEST);
+    result = curlx_dyn_addn(&tmp, STRCONST("Host: "));
+    if(!result && ipv6)
+      result = curlx_dyn_addn(&tmp, STRCONST("["));
+    if(!result)
+      result = curlx_dyn_add(&tmp, data->state.origin->hostname);
+    if(!result && ipv6)
+      result = curlx_dyn_addn(&tmp, STRCONST("]"));
+    if(!result &&
+       ((data->state.origin->port != data->state.origin->scheme->defport) ||
+       (data->state.origin->scheme->family != conn->scheme->family))) {
+      result = curlx_dyn_addf(&tmp, ":%u", data->state.origin->port);
+    }
 
-    if(!aptr->host)
-      /* without Host: we cannot make a nice request */
-      return CURLE_OUT_OF_MEMORY;
+    aptr->host = result ? NULL : curlx_dyn_take(&tmp, &hlen);
+    curlx_dyn_free(&tmp);
+    return result;
   }
   return CURLE_OK;
 }
@@ -2896,8 +2906,11 @@ static CURLcode http_add_hd(struct Curl_easy *data,
     break;
 
   case H1_HD_HOST:
-    if(data->state.aptr.host)
+    if(data->state.aptr.host) {
       result = curlx_dyn_add(req, data->state.aptr.host);
+      if(!result)
+        result = curlx_dyn_addn(req, STRCONST("\r\n"));
+    }
     break;
 
 #ifndef CURL_DISABLE_PROXY
diff --git a/lib/http_aws_sigv4.c b/lib/http_aws_sigv4.c
index 9c80c1ea9b..a1b1120964 100644
--- a/lib/http_aws_sigv4.c
+++ b/lib/http_aws_sigv4.c
@@ -401,11 +401,8 @@ static CURLcode make_headers(struct Curl_easy *data,
   if(!Curl_checkheaders(data, STRCONST("Host"))) {
     char *fullhost;
 
-    if(data->state.aptr.host) {
-      /* remove /r/n as the separator for canonical request must be '\n' */
-      size_t pos = strcspn(data->state.aptr.host, "\n\r");
-      fullhost = curlx_memdup0(data->state.aptr.host, pos);
-    }
+    if(data->state.aptr.host)
+      fullhost = curlx_strdup(data->state.aptr.host);
     else
       fullhost = curl_maprintf("host:%s", hostname);
 
diff --git a/lib/url.c b/lib/url.c
index de5111920a..a95e3581b4 100644
--- a/lib/url.c
+++ b/lib/url.c
@@ -1856,14 +1856,16 @@ static CURLcode parse_connect_to_string(struct Curl_easy *data,
     /* check whether the URL's hostname matches. Use the URL hostname
      * when it was an IPv6 address. Otherwise use the connection's hostname
      * that has IDN conversion. */
-    const char *hostname_to_match = (dest->user_hostname[0] == '[') ?
-      dest->user_hostname : dest->hostname;
-    size_t hlen = strlen(hostname_to_match);
-    host_match = curl_strnequal(ptr, hostname_to_match, hlen);
-    ptr += hlen;
-
-    host_match = host_match && *ptr == ':';
-    ptr++;
+    size_t hlen = strlen(dest->hostname);
+    host_match = curl_strnequal(ptr, dest->hostname, hlen);
+    if(!host_match && (dest->user_hostname != dest->hostname)) {
+      /* hostname was normalized, could be IPv6 or IDN */
+      hlen = strlen(dest->user_hostname);
+      host_match = curl_strnequal(ptr, dest->user_hostname, hlen);
+    }
+    host_match = host_match && ptr[hlen] == ':';
+    if(host_match)
+      ptr += hlen + 1;
   }
 
   if(host_match) {
diff --git a/lib/vssh/libssh.c b/lib/vssh/libssh.c
index 1ff7714af0..93be7ca21f 100644
--- a/lib/vssh/libssh.c
+++ b/lib/vssh/libssh.c
@@ -2585,6 +2585,8 @@ static CURLcode myssh_connect(struct Curl_easy *data, bool *done)
     return CURLE_FAILED_INIT;
   }
 
+  /* For ipv6 origins, use the `user_hostname` that has the "[]" enclosure.
+   * Otherwise, use `hostname` that is IDN converted. */
   rc = ssh_options_set(sshc->ssh_session, SSH_OPTIONS_HOST,
                        conn->origin->ipv6 ?
                        conn->origin->user_hostname : conn->origin->hostname);