diff --git a/tableauserverclient/server/endpoint/__init__.py b/tableauserverclient/server/endpoint/__init__.py
index 63d69510c..d9dca0f42 100644
--- a/tableauserverclient/server/endpoint/__init__.py
+++ b/tableauserverclient/server/endpoint/__init__.py
@@ -1,7 +1,7 @@
 from .auth_endpoint import Auth
 from .datasources_endpoint import Datasources
 from .endpoint import Endpoint
-from .exceptions import ServerResponseError, MissingRequiredFieldError
+from .exceptions import ServerResponseError, MissingRequiredFieldError, ServerInfoEndpointNotFoundError
 from .groups_endpoint import Groups
 from .projects_endpoint import Projects
 from .schedules_endpoint import Schedules
diff --git a/tableauserverclient/server/endpoint/exceptions.py b/tableauserverclient/server/endpoint/exceptions.py
index 7907a6dab..3eadd5ce5 100644
--- a/tableauserverclient/server/endpoint/exceptions.py
+++ b/tableauserverclient/server/endpoint/exceptions.py
@@ -24,3 +24,7 @@ def from_response(cls, resp):
 
 class MissingRequiredFieldError(Exception):
     pass
+
+
+class ServerInfoEndpointNotFoundError(Exception):
+    pass
diff --git a/tableauserverclient/server/endpoint/server_info_endpoint.py b/tableauserverclient/server/endpoint/server_info_endpoint.py
index 1fb17f26f..d6b2b7d96 100644
--- a/tableauserverclient/server/endpoint/server_info_endpoint.py
+++ b/tableauserverclient/server/endpoint/server_info_endpoint.py
@@ -1,4 +1,5 @@
 from .endpoint import Endpoint
+from .exceptions import ServerResponseError, ServerInfoEndpointNotFoundError
 from ...models import ServerInfoItem
 import logging
 
@@ -12,6 +13,11 @@ def baseurl(self):
 
     def get(self):
         """ Retrieve the server info for the server.  This is an unauthenticated call """
-        server_response = self.get_unauthenticated_request(self.baseurl)
+        try:
+            server_response = self.get_unauthenticated_request(self.baseurl)
+        except ServerResponseError as e:
+            if e.code == "404003":
+                raise ServerInfoEndpointNotFoundError
+
         server_info = ServerInfoItem.from_response(server_response.content)
         return server_info
diff --git a/tableauserverclient/server/server.py b/tableauserverclient/server/server.py
index 2cb08a892..b233377fe 100644
--- a/tableauserverclient/server/server.py
+++ b/tableauserverclient/server/server.py
@@ -1,8 +1,19 @@
+import xml.etree.ElementTree as ET
+
 from .exceptions import NotSignedInError
-from .endpoint import Sites, Views, Users, Groups, Workbooks, Datasources, Projects, Auth, Schedules, ServerInfo
+from .endpoint import Sites, Views, Users, Groups, Workbooks, Datasources, Projects, Auth, \
+    Schedules, ServerInfo, ServerInfoEndpointNotFoundError
 
 import requests
 
+_PRODUCT_TO_REST_VERSION = {
+    '10.0': '2.3',
+    '9.3': '2.2',
+    '9.2': '2.1',
+    '9.1': '2.0',
+    '9.0': '2.0'
+}
+
 
 class Server(object):
     class PublishMode:
@@ -47,6 +58,29 @@ def _set_auth(self, site_id, user_id, auth_token):
         self._user_id = user_id
         self._auth_token = auth_token
 
+    def _get_legacy_version(self):
+        response = self._session.get(self.server_address + "/auth?format=xml")
+        info_xml = ET.fromstring(response.content)
+        prod_version = info_xml.find('.//product_version').text
+        version = _PRODUCT_TO_REST_VERSION.get(prod_version, '2.1')  # 2.1
+        return version
+
+    def _determine_highest_version(self):
+        try:
+            old_version = self.version
+            self.version = "2.4"
+            version = self.server_info.get().rest_api_version
+        except ServerInfoEndpointNotFoundError:
+            version = self._get_legacy_version()
+
+        finally:
+            self.version = old_version
+
+        return version
+
+    def use_highest_version(self):
+        self.version = self._determine_highest_version()
+
     @property
     def baseurl(self):
         return "{0}/api/{1}".format(self._server_address, str(self.version))
diff --git a/test/assets/server_info_404.xml b/test/assets/server_info_404.xml
new file mode 100644
index 000000000..a23abf9ae
--- /dev/null
+++ b/test/assets/server_info_404.xml
@@ -0,0 +1,7 @@
+<?xml version="1.0" encoding="UTF-8"?>
+<tsResponse xmlns="http://tableau.com/api" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:schemaLocation="http://tableau.com/api http://tableau.com/api/ts-api-2.3.xsd">
+  <error code="404003">
+    <summary>Resource Not Found</summary>
+    <detail>Unknown resource '/2.4/serverInfo' specified in URI.</detail>
+  </error>
+</tsResponse>
diff --git a/test/assets/server_info_auth_info.xml b/test/assets/server_info_auth_info.xml
new file mode 100644
index 000000000..58d9c5baf
--- /dev/null
+++ b/test/assets/server_info_auth_info.xml
@@ -0,0 +1,12 @@
+<authinfo>
+<version version="0.31">
+<api_version>0.31</api_version>
+<server_api_version>0.31</server_api_version>
+<document_version>9.2</document_version>
+<product_version>9.3</product_version>
+<external_version>9.3.4</external_version>
+<build>hello.16.1106.2025</build>
+<publishing_method>unrestricted</publishing_method>
+<mobile_api_version>2.6</mobile_api_version>
+</version>
+</authinfo>
diff --git a/test/test_server_info.py b/test/test_server_info.py
index 03e39210f..084e6c91f 100644
--- a/test/test_server_info.py
+++ b/test/test_server_info.py
@@ -6,21 +6,48 @@
 TEST_ASSET_DIR = os.path.join(os.path.dirname(__file__), 'assets')
 
 SERVER_INFO_GET_XML = os.path.join(TEST_ASSET_DIR, 'server_info_get.xml')
+SERVER_INFO_404 = os.path.join(TEST_ASSET_DIR, 'server_info_404.xml')
+SERVER_INFO_AUTH_INFO_XML = os.path.join(TEST_ASSET_DIR, 'server_info_auth_info.xml')
 
 
 class ServerInfoTests(unittest.TestCase):
     def setUp(self):
         self.server = TSC.Server('http://test')
-        self.server.version = '2.4'
         self.baseurl = self.server.server_info.baseurl
 
     def test_server_info_get(self):
         with open(SERVER_INFO_GET_XML, 'rb') as f:
             response_xml = f.read().decode('utf-8')
         with requests_mock.mock() as m:
-            m.get(self.baseurl, text=response_xml)
+            self.server.version = '2.4'
+            m.get(self.server.server_info.baseurl, text=response_xml)
             actual = self.server.server_info.get()
 
             self.assertEqual('10.1.0', actual.product_version)
             self.assertEqual('10100.16.1024.2100', actual.build_number)
             self.assertEqual('2.4', actual.rest_api_version)
+
+    def test_server_info_use_highest_version_downgrades(self):
+        with open(SERVER_INFO_AUTH_INFO_XML, 'rb') as f:
+            # This is the auth.xml endpoint present back to 9.0 Servers
+            auth_response_xml = f.read().decode('utf-8')
+        with open(SERVER_INFO_404, 'rb') as f:
+            # 10.1 serverInfo response
+            si_response_xml = f.read().decode('utf-8')
+        with requests_mock.mock() as m:
+            # Return a 404 for serverInfo so we can pretend this is an old Server
+            m.get(self.server.server_address + "/api/2.4/serverInfo", text=si_response_xml, status_code=404)
+            m.get(self.server.server_address + "/auth?format=xml", text=auth_response_xml)
+            self.server.use_highest_version()
+            self.assertEqual(self.server.version, '2.2')
+
+    def test_server_info_use_highest_version_upgrades(self):
+        with open(SERVER_INFO_GET_XML, 'rb') as f:
+            si_response_xml = f.read().decode('utf-8')
+        with requests_mock.mock() as m:
+            m.get(self.server.server_address + "/api/2.4/serverInfo", text=si_response_xml)
+            # Pretend we're old
+            self.server.version = '2.0'
+            self.server.use_highest_version()
+            # Did we upgrade to 2.4?
+            self.assertEqual(self.server.version, '2.4')