diff --git a/automated install/basic-install.sh b/automated install/basic-install.sh
index 762ee110..4c9352b8 100755
--- a/automated install/basic-install.sh	
+++ b/automated install/basic-install.sh	
@@ -1018,9 +1018,9 @@ valid_ip() {
     local stat=1
 
     # Regex matching one IPv4 component, i.e. an integer from 0 to 255.
-    local ipv4elem="(25[0-5]|2[0-4][0-9]|1[0-9][0-9]|[1-9][0-9]?|0)";
+    local ipv4elem="(25[0-5]|2[0-4][0-9]|1[0-9][0-9]|[0-9]{1,2})";
     # Regex matching an optional port beginning with # matching optional port number starting '#' with range of 1 to 65536
-    local portelem="(#([1-9]|[1-8][0-9]|9[0-9]|[1-8][0-9]{2}|9[0-8][0-9]|99[0-9]|[1-8][0-9]{3}|9[0-8][0-9]{2}|99[0-8][0-9]|999[0-9]|[1-5][0-9]{4}|6[0-4][0-9]{3}|65[0-4][0-9]{2}|655[0-2][0-9]|6553[0-6]))?"
+    local portelem="(:(6553[0-5]|655[0-2][0-9]|65[0-4][0-9]{2}|6[0-4][0-9]{3}|[1-5][0-9]{4}|[0-9]{1,4}))?";
     # Build a full IPv4 regex from the above subexpressions
     local regex="^${ipv4elem}\.${ipv4elem}\.${ipv4elem}\.${ipv4elem}${portelem}$"
 
diff --git a/test/test_automated_install.py b/test/test_automated_install.py
index f6b5a87e..20dadc26 100644
--- a/test/test_automated_install.py
+++ b/test/test_automated_install.py
@@ -524,43 +524,37 @@ def test_IPv6_ULA_GUA_test(Pihole):
     assert expected_stdout in detectPlatform.stdout
 
 
-def test_validate_ip_valid(Pihole):
-    '''
-    Given a valid IP address, valid_ip returns success
-    '''
-
-    output = Pihole.run('''
-    source /opt/pihole/basic-install.sh
-    valid_ip "192.168.1.1"
-    ''')
-
-    assert output.rc == 0
-
-
-def test_validate_ip_invalid_octet(Pihole):
-    '''
-    Given an invalid IP address (large octet), valid_ip returns an error
-    '''
-
-    output = Pihole.run('''
-    source /opt/pihole/basic-install.sh
-    valid_ip "1092.168.1.1"
-    ''')
-
-    assert output.rc == 1
-
-
-def test_validate_ip_invalid_letters(Pihole):
-    '''
-    Given an invalid IP address (contains letters), valid_ip returns an error
-    '''
-
-    output = Pihole.run('''
-    source /opt/pihole/basic-install.sh
-    valid_ip "not an IP"
-    ''')
-
-    assert output.rc == 1
+def test_validate_ip(Pihole):
+    '''
+    Tests valid_ip for various IP addresses
+    '''
+
+    def test_address(addr, success=True):
+        output = Pihole.run('''
+        source /opt/pihole/basic-install.sh
+        valid_ip "{addr}"
+        '''.format(addr=addr))
+
+        assert output.rc == 0 if success else 1
+
+    test_address('192.168.1.1')
+    test_address('127.0.0.1')
+    test_address('255.255.255.255')
+    test_address('255.255.255.256', False)
+    test_address('255.255.256.255', False)
+    test_address('255.256.255.255', False)
+    test_address('256.255.255.255', False)
+    test_address('1092.168.1.1', False)
+    test_address('not an IP', False)
+    test_address('8.8.8.8:', False)
+    test_address('8.8.8.8:0')
+    test_address('8.8.8.8:1')
+    test_address('8.8.8.8:42')
+    test_address('8.8.8.8:888')
+    test_address('8.8.8.8:1337')
+    test_address('8.8.8.8:65535')
+    test_address('8.8.8.8:65536', False)
+    test_address('8.8.8.8:-1', False)
 
 
 def test_os_check_fails(Pihole):