diff --git a/x-pack/plugins/security_solution/common/endpoint/schema/trusted_apps.ts b/x-pack/plugins/security_solution/common/endpoint/schema/trusted_apps.ts
index 03cbe53f60320..9858f2a72c2d0 100644
--- a/x-pack/plugins/security_solution/common/endpoint/schema/trusted_apps.ts
+++ b/x-pack/plugins/security_solution/common/endpoint/schema/trusted_apps.ts
@@ -6,7 +6,7 @@
  */
 
 import { schema } from '@kbn/config-schema';
-import { ConditionEntry, ConditionEntryField, OperatingSystem, OperatorEntryField } from '../types';
+import { ConditionEntry, ConditionEntryField, OperatingSystem } from '../types';
 import { getDuplicateFields, isValidHash } from '../service/trusted_apps/validations';
 
 export const DeleteTrustedAppsRequestSchema = {
@@ -29,17 +29,13 @@ export const GetTrustedAppsRequestSchema = {
   }),
 };
 
-const ConditionEntryTypeSchema = schema.literal('match');
-// when field === PATH -> operator in ('included', 'wildcard_caseless') else operator === 'included'
-const ConditionEntryOperatorSchema = schema.conditional(
+const ConditionEntryTypeSchema = schema.conditional(
   schema.siblingRef('field'),
   ConditionEntryField.PATH,
-  schema.oneOf([
-    schema.literal(OperatorEntryField.included),
-    schema.literal(OperatorEntryField.wildcard_caseless),
-  ]),
-  schema.literal(OperatorEntryField.included)
+  schema.oneOf([schema.literal('match'), schema.literal('wildcard')]),
+  schema.literal('match')
 );
+const ConditionEntryOperatorSchema = schema.literal('included' as ConditionEntry['operator']);
 
 /*
  * A generic Entry schema to be used for a specific entry schema depending on the OS
diff --git a/x-pack/plugins/security_solution/common/endpoint/types/trusted_apps.ts b/x-pack/plugins/security_solution/common/endpoint/types/trusted_apps.ts
index 371f7848b6bb4..3c854dbb7bd72 100644
--- a/x-pack/plugins/security_solution/common/endpoint/types/trusted_apps.ts
+++ b/x-pack/plugins/security_solution/common/endpoint/types/trusted_apps.ts
@@ -7,6 +7,8 @@
 
 import { TypeOf } from '@kbn/config-schema';
 import { ApplicationStart } from 'kibana/public';
+
+import { Entry } from '../../../../lists/common/schemas/types/entries';
 import {
   DeleteTrustedAppsRequestSchema,
   GetOneTrustedAppRequestSchema,
@@ -69,14 +71,15 @@ export enum ConditionEntryField {
   SIGNER = 'process.Ext.code_signature',
 }
 
-export enum OperatorEntryField {
-  included = 'included',
-  wildcard_caseless = 'wildcard_caseless',
+export enum OperatorFieldIds {
+  is = 'is',
+  matches = 'matches',
 }
+
 export interface ConditionEntry<T extends ConditionEntryField = ConditionEntryField> {
   field: T;
-  type: 'match';
-  operator: keyof typeof OperatorEntryField;
+  type: Entry['type'];
+  operator: 'included';
   value: string;
 }
 
diff --git a/x-pack/plugins/security_solution/common/shared_imports.ts b/x-pack/plugins/security_solution/common/shared_imports.ts
index aaae0d4dc25ef..f02cc472e9f60 100644
--- a/x-pack/plugins/security_solution/common/shared_imports.ts
+++ b/x-pack/plugins/security_solution/common/shared_imports.ts
@@ -20,6 +20,7 @@ export {
   EntryExists,
   EntryMatch,
   EntryMatchAny,
+  EntriesMatchWildcardCaseless,
   EntryNested,
   EntryList,
   EntriesArray,
@@ -38,6 +39,7 @@ export {
   nestedEntryItem,
   entriesMatch,
   entriesMatchAny,
+  entriesMatchWildcardCaseless,
   entriesExists,
   entriesList,
   namespaceType,
diff --git a/x-pack/plugins/security_solution/public/common/components/exceptions/types.ts b/x-pack/plugins/security_solution/public/common/components/exceptions/types.ts
index c7a125daa54f8..7bce9f0b557b2 100644
--- a/x-pack/plugins/security_solution/public/common/components/exceptions/types.ts
+++ b/x-pack/plugins/security_solution/public/common/components/exceptions/types.ts
@@ -15,6 +15,7 @@ import {
   Entry,
   EntryMatch,
   EntryMatchAny,
+  EntriesMatchWildcardCaseless,
   EntryExists,
   ExceptionListItemSchema,
   CreateExceptionListItemSchema,
@@ -92,6 +93,7 @@ export interface EmptyNestedEntry {
   type: OperatorTypeEnum.NESTED;
   entries: Array<
     | (EntryMatch & { id?: string })
+    | (EntriesMatchWildcardCaseless & { id?: string })
     | (EntryMatchAny & { id?: string })
     | (EntryExists & { id?: string })
   >;
@@ -108,6 +110,7 @@ export type BuilderEntryNested = Omit<EntryNested, 'entries'> & {
   id?: string;
   entries: Array<
     | (EntryMatch & { id?: string })
+    | (EntriesMatchWildcardCaseless & { id?: string })
     | (EntryMatchAny & { id?: string })
     | (EntryExists & { id?: string })
   >;
diff --git a/x-pack/plugins/security_solution/public/management/pages/trusted_apps/view/components/condition_entry_input/index.tsx b/x-pack/plugins/security_solution/public/management/pages/trusted_apps/view/components/condition_entry_input/index.tsx
index 21a472d80a955..1f3fed2fd4b61 100644
--- a/x-pack/plugins/security_solution/public/management/pages/trusted_apps/view/components/condition_entry_input/index.tsx
+++ b/x-pack/plugins/security_solution/public/management/pages/trusted_apps/view/components/condition_entry_input/index.tsx
@@ -20,7 +20,7 @@ import {
 import {
   ConditionEntry,
   ConditionEntryField,
-  OperatorEntryField,
+  OperatorFieldIds,
   OperatingSystem,
 } from '../../../../../../../common/endpoint/types';
 
@@ -79,10 +79,10 @@ const InputItem = styled.div`
   vertical-align: baseline;
 `;
 
-const operatorOptions = (Object.keys(OperatorEntryField) as OperatorEntryField[]).map((value) => ({
+const operatorOptions = (Object.keys(OperatorFieldIds) as OperatorFieldIds[]).map((value) => ({
   dropdownDisplay: OPERATOR_TITLES[value],
   inputDisplay: OPERATOR_TITLES[value],
-  value,
+  value: value === 'matches' ? 'wildcard' : 'match',
 }));
 
 export const ConditionEntryInput = memo<ConditionEntryInputProps>(
@@ -144,7 +144,7 @@ export const ConditionEntryInput = memo<ConditionEntryInputProps>(
     );
 
     const handleOperatorUpdate = useCallback(
-      (newOperator) => onChange({ ...entry, operator: newOperator }, entry),
+      (newOperator) => onChange({ ...entry, type: newOperator }, entry),
       [entry, onChange]
     );
 
@@ -174,13 +174,13 @@ export const ConditionEntryInput = memo<ConditionEntryInputProps>(
               <EuiSuperSelect
                 options={operatorOptions}
                 onChange={handleOperatorUpdate}
-                valueOfSelected={entry.operator}
+                valueOfSelected={entry.type}
                 data-test-subj={getTestId('operator')}
               />
             ) : (
               <EuiFieldText
                 name="operator"
-                value={OPERATOR_TITLES.included}
+                value={OPERATOR_TITLES.is}
                 data-test-subj={getTestId('operator')}
                 readOnly
               />
diff --git a/x-pack/plugins/security_solution/public/management/pages/trusted_apps/view/components/trusted_app_card/index.tsx b/x-pack/plugins/security_solution/public/management/pages/trusted_apps/view/components/trusted_app_card/index.tsx
index aadee204dab14..8289792b81f89 100644
--- a/x-pack/plugins/security_solution/public/management/pages/trusted_apps/view/components/trusted_app_card/index.tsx
+++ b/x-pack/plugins/security_solution/public/management/pages/trusted_apps/view/components/trusted_app_card/index.tsx
@@ -45,7 +45,7 @@ const getEntriesColumnDefinitions = (): Array<EuiTableFieldDataColumnType<Entry>
     truncateText: true,
     textOnly: true,
     width: '30%',
-    render(field: Entry['field'], entry: Entry) {
+    render(field: Entry['field'], _entry: Entry) {
       return CONDITION_FIELD_TITLE[field];
     },
   },
@@ -55,8 +55,8 @@ const getEntriesColumnDefinitions = (): Array<EuiTableFieldDataColumnType<Entry>
     sortable: false,
     truncateText: true,
     width: '20%',
-    render(field: Entry['operator'], entry: Entry) {
-      return OPERATOR_TITLES[field];
+    render(_field: Entry['operator'], entry: Entry) {
+      return entry.type === 'wildcard' ? OPERATOR_TITLES.matches : OPERATOR_TITLES.is;
     },
   },
   {
diff --git a/x-pack/plugins/security_solution/public/management/pages/trusted_apps/view/translations.ts b/x-pack/plugins/security_solution/public/management/pages/trusted_apps/view/translations.ts
index 7071022fb893f..f955e7b7dc568 100644
--- a/x-pack/plugins/security_solution/public/management/pages/trusted_apps/view/translations.ts
+++ b/x-pack/plugins/security_solution/public/management/pages/trusted_apps/view/translations.ts
@@ -11,7 +11,7 @@ import {
   MacosLinuxConditionEntry,
   WindowsConditionEntry,
   ConditionEntryField,
-  OperatorEntryField,
+  OperatorFieldIds,
 } from '../../../../../common/endpoint/types';
 
 export { OS_TITLES } from '../../../common/translations';
@@ -52,19 +52,13 @@ export const CONDITION_FIELD_DESCRIPTION: { [K in ConditionEntryField]: string }
   ),
 };
 
-export const OPERATOR_TITLES: { [K in OperatorEntryField]: string } = {
-  [OperatorEntryField.included]: i18n.translate(
-    'xpack.securitySolution.trustedapps.card.operator.is',
-    {
-      defaultMessage: 'is',
-    }
-  ),
-  [OperatorEntryField.wildcard_caseless]: i18n.translate(
-    'xpack.securitySolution.trustedapps.card.operator.matches',
-    {
-      defaultMessage: 'matches',
-    }
-  ),
+export const OPERATOR_TITLES: { [K in OperatorFieldIds]: string } = {
+  is: i18n.translate('xpack.securitySolution.trustedapps.card.operator.is', {
+    defaultMessage: 'is',
+  }),
+  matches: i18n.translate('xpack.securitySolution.trustedapps.card.operator.matches', {
+    defaultMessage: 'matches',
+  }),
 };
 
 export const PROPERTY_TITLES: Readonly<
diff --git a/x-pack/plugins/security_solution/server/endpoint/routes/trusted_apps/mapping.ts b/x-pack/plugins/security_solution/server/endpoint/routes/trusted_apps/mapping.ts
index cae1d9c27eb7f..a0ccef78ea0cf 100644
--- a/x-pack/plugins/security_solution/server/endpoint/routes/trusted_apps/mapping.ts
+++ b/x-pack/plugins/security_solution/server/endpoint/routes/trusted_apps/mapping.ts
@@ -9,12 +9,13 @@ import uuid from 'uuid';
 
 import { OsType } from '../../../../../lists/common/schemas';
 import {
+  Entry,
   EntriesArray,
   EntryMatch,
+  EntriesMatchWildcardCaseless,
   EntryNested,
   ExceptionListItemSchema,
   NestedEntriesArray,
-  Operator,
 } from '../../../../../lists/common';
 import { ENDPOINT_TRUSTED_APPS_LIST_ID } from '../../../../../lists/common/constants';
 import {
@@ -27,7 +28,6 @@ import {
   EffectScope,
   NewTrustedApp,
   OperatingSystem,
-  OperatorEntryField,
   TrustedApp,
   UpdateTrustedApp,
 } from '../../../../common/endpoint/types';
@@ -48,17 +48,18 @@ const OPERATING_SYSTEM_TO_OS_TYPE: Mapping<OperatingSystem, OsType> = {
 };
 
 const POLICY_REFERENCE_PREFIX = 'policy:';
+const OPERATOR_VALUE = 'included';
 
 const filterUndefined = <T>(list: Array<T | undefined>): T[] => {
   return list.filter((item: T | undefined): item is T => item !== undefined);
 };
 
-export const createConditionEntry = <T extends ConditionEntryField, O extends OperatorEntryField>(
+export const createConditionEntry = <T extends ConditionEntryField>(
   field: T,
-  operator: O,
+  type: Entry['type'],
   value: string
 ): ConditionEntry<T> => {
-  return { field, value, type: 'match', operator };
+  return { field, value, type, operator: OPERATOR_VALUE };
 };
 
 export const tagsToEffectScope = (tags: string[]): EffectScope => {
@@ -76,46 +77,26 @@ export const tagsToEffectScope = (tags: string[]): EffectScope => {
   }
 };
 
-type TrustedAppsEntriesArray = Omit<EntriesArray, 'operator'> & {
-  operator: Operator | 'wildcard_caseless';
-};
-
-export const entriesToConditionEntriesMap = (
-  entries: TrustedAppsEntriesArray
-): ConditionEntriesMap => {
+export const entriesToConditionEntriesMap = (entries: EntriesArray): ConditionEntriesMap => {
   return entries.reduce((result, entry) => {
     if (entry.field.startsWith('process.hash') && entry.type === 'match') {
       return {
         ...result,
         [ConditionEntryField.HASH]: createConditionEntry(
           ConditionEntryField.HASH,
-          OperatorEntryField.included,
-          entry.value
-        ),
-      };
-    } else if (
-      entry.field === 'process.executable.caseless' &&
-      entry.type === 'match' &&
-      entry.operator === OperatorEntryField.wildcard_caseless
-    ) {
-      return {
-        ...result,
-        [ConditionEntryField.PATH]: createConditionEntry(
-          ConditionEntryField.PATH,
-          OperatorEntryField.wildcard_caseless,
+          entry.type,
           entry.value
         ),
       };
     } else if (
       entry.field === 'process.executable.caseless' &&
-      entry.type === 'match' &&
-      entry.operator === OperatorEntryField.included
+      (entry.type === 'match' || entry.type === 'wildcard')
     ) {
       return {
         ...result,
         [ConditionEntryField.PATH]: createConditionEntry(
           ConditionEntryField.PATH,
-          OperatorEntryField.included,
+          entry.type,
           entry.value
         ),
       };
@@ -129,7 +110,7 @@ export const entriesToConditionEntriesMap = (
           ...result,
           [ConditionEntryField.SIGNER]: createConditionEntry(
             ConditionEntryField.SIGNER,
-            OperatorEntryField.included,
+            entry.type,
             subjectNameCondition.value
           ),
         };
@@ -200,12 +181,15 @@ const hashType = (hash: string): 'md5' | 'sha256' | 'sha1' | undefined => {
   }
 };
 
-export const createEntryMatch = (
+export const createEntryMatch = (field: string, value: string): EntryMatch => {
+  return { field, value, type: 'match', operator: OPERATOR_VALUE };
+};
+
+export const createEntryMatchWildcardCaseless = (
   field: string,
-  operator: OperatorEntryField,
   value: string
-): EntryMatch => {
-  return { field, value, type: 'match', operator };
+): EntriesMatchWildcardCaseless => {
+  return { field, value, type: 'wildcard', operator: OPERATOR_VALUE };
 };
 
 export const createEntryNested = (field: string, entries: NestedEntriesArray): EntryNested => {
@@ -225,29 +209,20 @@ export const conditionEntriesToEntries = (conditionEntries: ConditionEntry[]): E
     if (conditionEntry.field === ConditionEntryField.HASH) {
       return createEntryMatch(
         `process.hash.${hashType(conditionEntry.value)}`,
-        OperatorEntryField.included,
         conditionEntry.value.toLowerCase()
       );
     } else if (conditionEntry.field === ConditionEntryField.SIGNER) {
       return createEntryNested(`process.Ext.code_signature`, [
-        createEntryMatch('trusted', OperatorEntryField.included, 'true'),
-        createEntryMatch('subject_name', OperatorEntryField.included, conditionEntry.value),
+        createEntryMatch('trusted', 'true'),
+        createEntryMatch('subject_name', conditionEntry.value),
       ]);
     } else if (
       conditionEntry.field === ConditionEntryField.PATH &&
-      conditionEntry.operator === OperatorEntryField.wildcard_caseless
+      conditionEntry.type === 'wildcard'
     ) {
-      return createEntryMatch(
-        `process.executable.caseless`,
-        OperatorEntryField.wildcard_caseless,
-        conditionEntry.value
-      );
+      return createEntryMatchWildcardCaseless(`process.executable.caseless`, conditionEntry.value);
     } else {
-      return createEntryMatch(
-        `process.executable.caseless`,
-        OperatorEntryField.included,
-        conditionEntry.value
-      );
+      return createEntryMatch(`process.executable.caseless`, conditionEntry.value);
     }
   });
 };