diff --git a/helper/schema/schema.go b/helper/schema/schema.go
index 881b2ebba2..78cfb546c7 100644
--- a/helper/schema/schema.go
+++ b/helper/schema/schema.go
@@ -770,7 +770,7 @@ func (m schemaMap) internalValidate(topSchemaMap schemaMap, attrsOnly bool) erro
 		}
 
 		if len(v.ConflictsWith) > 0 {
-			err := checkKeysAgainstSchemaFlags(k, v.ConflictsWith, topSchemaMap)
+			err := checkKeysAgainstSchemaFlags(k, v.ConflictsWith, topSchemaMap, v)
 			if err != nil {
 				return fmt.Errorf("ConflictsWith: %+v", err)
 			}
@@ -784,14 +784,14 @@ func (m schemaMap) internalValidate(topSchemaMap schemaMap, attrsOnly bool) erro
 		}
 
 		if len(v.ExactlyOneOf) > 0 {
-			err := checkKeysAgainstSchemaFlags(k, v.ExactlyOneOf, topSchemaMap)
+			err := checkKeysAgainstSchemaFlags(k, v.ExactlyOneOf, topSchemaMap, v)
 			if err != nil {
 				return fmt.Errorf("ExactlyOneOf: %+v", err)
 			}
 		}
 
 		if len(v.AtLeastOneOf) > 0 {
-			err := checkKeysAgainstSchemaFlags(k, v.AtLeastOneOf, topSchemaMap)
+			err := checkKeysAgainstSchemaFlags(k, v.AtLeastOneOf, topSchemaMap, v)
 			if err != nil {
 				return fmt.Errorf("AtLeastOneOf: %+v", err)
 			}
@@ -860,14 +860,20 @@ func (m schemaMap) internalValidate(topSchemaMap schemaMap, attrsOnly bool) erro
 	return nil
 }
 
-func checkKeysAgainstSchemaFlags(k string, keys []string, topSchemaMap schemaMap) error {
+func checkKeysAgainstSchemaFlags(k string, keys []string, topSchemaMap schemaMap, self *Schema) error {
 	for _, key := range keys {
 		parts := strings.Split(key, ".")
 		sm := topSchemaMap
 		var target *Schema
 		for _, part := range parts {
-			// Skip index fields
-			if _, err := strconv.Atoi(part); err == nil {
+			// Skip index fields if 0
+			partInt, err := strconv.Atoi(part)
+
+			if err == nil {
+				if partInt != 0 {
+					return fmt.Errorf("%s configuration block reference (%s) can only use the .0. index for TypeList and MaxItems: 1 configuration blocks", k, key)
+				}
+
 				continue
 			}
 
@@ -876,13 +882,27 @@ func checkKeysAgainstSchemaFlags(k string, keys []string, topSchemaMap schemaMap
 				return fmt.Errorf("%s references unknown attribute (%s) at part (%s)", k, key, part)
 			}
 
-			if subResource, ok := target.Elem.(*Resource); ok {
-				sm = schemaMap(subResource.Schema)
+			subResource, ok := target.Elem.(*Resource)
+
+			if !ok {
+				continue
+			}
+
+			if target.Type == TypeSet || target.MaxItems != 1 {
+				return fmt.Errorf("%s configuration block reference (%s) can only be used with TypeList and MaxItems: 1 configuration blocks", k, key)
 			}
+
+			sm = schemaMap(subResource.Schema)
 		}
+
 		if target == nil {
 			return fmt.Errorf("%s cannot find target attribute (%s), sm: %#v", k, key, sm)
 		}
+
+		if target == self {
+			return fmt.Errorf("%s cannot reference self (%s)", k, key)
+		}
+
 		if target.Required {
 			return fmt.Errorf("%s cannot contain Required attribute (%s)", k, key)
 		}
diff --git a/helper/schema/schema_test.go b/helper/schema/schema_test.go
index 2f21f536cc..87d1603255 100644
--- a/helper/schema/schema_test.go
+++ b/helper/schema/schema_test.go
@@ -3611,7 +3611,7 @@ func TestSchemaMap_InternalValidate(t *testing.T) {
 					},
 				},
 			},
-			false, // TODO: This should return an error as it will always error during runtime
+			true,
 		},
 
 		"ConflictsWith list index syntax with list configuration block existing attribute": {
@@ -3619,6 +3619,7 @@ func TestSchemaMap_InternalValidate(t *testing.T) {
 				"config_block_attr": &Schema{
 					Type:     TypeList,
 					Optional: true,
+					MaxItems: 1,
 					Elem: &Resource{
 						Schema: map[string]*Schema{
 							"nested_attr": &Schema{
@@ -3660,6 +3661,29 @@ func TestSchemaMap_InternalValidate(t *testing.T) {
 			true,
 		},
 
+		"ConflictsWith list index syntax with list configuration block missing MaxItems": {
+			map[string]*Schema{
+				"config_block_attr": &Schema{
+					Type:     TypeList,
+					Optional: true,
+					Elem: &Resource{
+						Schema: map[string]*Schema{
+							"nested_attr": &Schema{
+								Type:     TypeString,
+								Optional: true,
+							},
+						},
+					},
+				},
+				"test": &Schema{
+					Type:          TypeBool,
+					Optional:      true,
+					ConflictsWith: []string{"config_block_attr.0.missing_attr"},
+				},
+			},
+			true,
+		},
+
 		"ConflictsWith list index syntax with set configuration block existing attribute": {
 			map[string]*Schema{
 				"config_block_attr": &Schema{
@@ -3680,7 +3704,7 @@ func TestSchemaMap_InternalValidate(t *testing.T) {
 					ConflictsWith: []string{"config_block_attr.0.nested_attr"},
 				},
 			},
-			false, // TODO: This should return an error as sets cannot be indexed
+			true,
 		},
 
 		"ConflictsWith list index syntax with set configuration block missing attribute": {
@@ -3726,7 +3750,7 @@ func TestSchemaMap_InternalValidate(t *testing.T) {
 					ConflictsWith: []string{"config_block_attr.nested_attr"},
 				},
 			},
-			false, // TODO: This should return an error as validateConflictingAttributes will never error
+			true,
 		},
 
 		"ConflictsWith map key syntax with list configuration block self reference": {
@@ -3745,7 +3769,7 @@ func TestSchemaMap_InternalValidate(t *testing.T) {
 					},
 				},
 			},
-			false, // TODO: This should return an error as validateConflictingAttributes will never error
+			true,
 		},
 
 		"ConflictsWith map key syntax with set configuration block existing attribute": {
@@ -3768,7 +3792,7 @@ func TestSchemaMap_InternalValidate(t *testing.T) {
 					ConflictsWith: []string{"config_block_attr.nested_attr"},
 				},
 			},
-			false, // TODO: This should return an error as validateConflictingAttributes will never error and sets cannot be indexed
+			true,
 		},
 
 		"ConflictsWith map key syntax with set configuration block self reference": {
@@ -3787,7 +3811,7 @@ func TestSchemaMap_InternalValidate(t *testing.T) {
 					},
 				},
 			},
-			false, // TODO: This should return an error as validateConflictingAttributes will never error and sets cannot be indexed
+			true,
 		},
 
 		"ConflictsWith map key syntax with map attribute": {
@@ -3830,7 +3854,7 @@ func TestSchemaMap_InternalValidate(t *testing.T) {
 					ConflictsWith: []string{"test"},
 				},
 			},
-			false, // TODO: This should return an error as it will always error during runtime
+			true,
 		},
 
 		"Sub-resource invalid": {