diff --git a/api_docs/security_solution.json b/api_docs/security_solution.json
index aea50fdbfecaa..1e932a807d7d6 100644
--- a/api_docs/security_solution.json
+++ b/api_docs/security_solution.json
@@ -207,7 +207,7 @@
                 "description": [],
                 "source": {
                   "path": "x-pack/plugins/security_solution/public/plugin.tsx",
-                  "lineNumber": 353
+                  "lineNumber": 346
                 }
               },
               {
@@ -221,7 +221,7 @@
                 "description": [],
                 "source": {
                   "path": "x-pack/plugins/security_solution/public/plugin.tsx",
-                  "lineNumber": 353
+                  "lineNumber": 346
                 }
               }
             ],
@@ -229,7 +229,7 @@
             "returnComment": [],
             "source": {
               "path": "x-pack/plugins/security_solution/public/plugin.tsx",
-              "lineNumber": 353
+              "lineNumber": 346
             }
           },
           {
@@ -245,7 +245,7 @@
             "returnComment": [],
             "source": {
               "path": "x-pack/plugins/security_solution/public/plugin.tsx",
-              "lineNumber": 398
+              "lineNumber": 391
             }
           }
         ],
@@ -276,7 +276,7 @@
           "description": [],
           "source": {
             "path": "x-pack/plugins/security_solution/public/types.ts",
-            "lineNumber": 69
+            "lineNumber": 68
           },
           "signature": [
             "() => Promise<",
@@ -287,7 +287,7 @@
       ],
       "source": {
         "path": "x-pack/plugins/security_solution/public/types.ts",
-        "lineNumber": 68
+        "lineNumber": 67
       },
       "lifecycle": "setup",
       "initialIsOpen": true
@@ -301,7 +301,7 @@
       "children": [],
       "source": {
         "path": "x-pack/plugins/security_solution/public/types.ts",
-        "lineNumber": 72
+        "lineNumber": 71
       },
       "lifecycle": "start",
       "initialIsOpen": true
@@ -453,7 +453,7 @@
                 "description": [],
                 "source": {
                   "path": "x-pack/plugins/security_solution/server/plugin.ts",
-                  "lineNumber": 147
+                  "lineNumber": 145
                 }
               }
             ],
@@ -461,7 +461,7 @@
             "returnComment": [],
             "source": {
               "path": "x-pack/plugins/security_solution/server/plugin.ts",
-              "lineNumber": 147
+              "lineNumber": 145
             }
           },
           {
@@ -521,7 +521,7 @@
                 "description": [],
                 "source": {
                   "path": "x-pack/plugins/security_solution/server/plugin.ts",
-                  "lineNumber": 159
+                  "lineNumber": 157
                 }
               },
               {
@@ -535,7 +535,7 @@
                 "description": [],
                 "source": {
                   "path": "x-pack/plugins/security_solution/server/plugin.ts",
-                  "lineNumber": 159
+                  "lineNumber": 157
                 }
               }
             ],
@@ -543,7 +543,7 @@
             "returnComment": [],
             "source": {
               "path": "x-pack/plugins/security_solution/server/plugin.ts",
-              "lineNumber": 159
+              "lineNumber": 157
             }
           },
           {
@@ -582,7 +582,7 @@
                 "description": [],
                 "source": {
                   "path": "x-pack/plugins/security_solution/server/plugin.ts",
-                  "lineNumber": 341
+                  "lineNumber": 338
                 }
               },
               {
@@ -596,7 +596,7 @@
                 "description": [],
                 "source": {
                   "path": "x-pack/plugins/security_solution/server/plugin.ts",
-                  "lineNumber": 341
+                  "lineNumber": 338
                 }
               }
             ],
@@ -604,7 +604,7 @@
             "returnComment": [],
             "source": {
               "path": "x-pack/plugins/security_solution/server/plugin.ts",
-              "lineNumber": 341
+              "lineNumber": 338
             }
           },
           {
@@ -620,13 +620,13 @@
             "returnComment": [],
             "source": {
               "path": "x-pack/plugins/security_solution/server/plugin.ts",
-              "lineNumber": 423
+              "lineNumber": 412
             }
           }
         ],
         "source": {
           "path": "x-pack/plugins/security_solution/server/plugin.ts",
-          "lineNumber": 131
+          "lineNumber": 129
         },
         "initialIsOpen": false
       }
@@ -1484,7 +1484,7 @@
       "children": [],
       "source": {
         "path": "x-pack/plugins/security_solution/server/plugin.ts",
-        "lineNumber": 107
+        "lineNumber": 105
       },
       "lifecycle": "setup",
       "initialIsOpen": true
@@ -1498,7 +1498,7 @@
       "children": [],
       "source": {
         "path": "x-pack/plugins/security_solution/server/plugin.ts",
-        "lineNumber": 110
+        "lineNumber": 108
       },
       "lifecycle": "start",
       "initialIsOpen": true
diff --git a/x-pack/plugins/lists/common/constants.mock.ts b/x-pack/plugins/lists/common/constants.mock.ts
index 27e0fa29b1e55..177f0a4b291d5 100644
--- a/x-pack/plugins/lists/common/constants.mock.ts
+++ b/x-pack/plugins/lists/common/constants.mock.ts
@@ -51,6 +51,7 @@ export const OPERATOR_EXCLUDED = 'excluded';
 export const ENTRY_VALUE = 'some host name';
 export const MATCH = 'match';
 export const MATCH_ANY = 'match_any';
+export const WILDCARD = 'wildcard';
 export const MAX_IMPORT_PAYLOAD_BYTES = 9000000;
 export const IMPORT_BUFFER_SIZE = 1000;
 export const LIST = 'list';
diff --git a/x-pack/plugins/lists/common/schemas/common/schemas.ts b/x-pack/plugins/lists/common/schemas/common/schemas.ts
index f261e4e3eefa6..7e43e7dd5f4ab 100644
--- a/x-pack/plugins/lists/common/schemas/common/schemas.ts
+++ b/x-pack/plugins/lists/common/schemas/common/schemas.ts
@@ -287,6 +287,7 @@ export enum OperatorTypeEnum {
   NESTED = 'nested',
   MATCH = 'match',
   MATCH_ANY = 'match_any',
+  WILDCARD = 'wildcard',
   EXISTS = 'exists',
   LIST = 'list',
 }
diff --git a/x-pack/plugins/lists/common/schemas/types/endpoint/entry_match_wildcard.ts b/x-pack/plugins/lists/common/schemas/types/endpoint/entry_match_wildcard.ts
new file mode 100644
index 0000000000000..dfcaa963666de
--- /dev/null
+++ b/x-pack/plugins/lists/common/schemas/types/endpoint/entry_match_wildcard.ts
@@ -0,0 +1,21 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import * as t from 'io-ts';
+
+import { NonEmptyString } from '../../../shared_imports';
+import { operatorIncluded } from '../../common/schemas';
+
+export const endpointEntryMatchWildcard = t.exact(
+  t.type({
+    field: NonEmptyString,
+    operator: operatorIncluded,
+    type: t.keyof({ wildcard: null }),
+    value: NonEmptyString,
+  })
+);
+export type EndpointEntryMatchWildcard = t.TypeOf<typeof endpointEntryMatchWildcard>;
diff --git a/x-pack/plugins/lists/common/schemas/types/entries.ts b/x-pack/plugins/lists/common/schemas/types/entries.ts
index 277751bf1c271..26cfed568cea8 100644
--- a/x-pack/plugins/lists/common/schemas/types/entries.ts
+++ b/x-pack/plugins/lists/common/schemas/types/entries.ts
@@ -12,12 +12,28 @@ import { entriesMatch } from './entry_match';
 import { entriesExists } from './entry_exists';
 import { entriesList } from './entry_list';
 import { entriesNested } from './entry_nested';
+import { entriesMatchWildcard } from './entry_match_wildcard';
 
-export const entry = t.union([entriesMatch, entriesMatchAny, entriesList, entriesExists]);
+// NOTE: Type nested is not included here to denote it's non-recursive nature.
+// So a nested entry is really just a collection of `Entry` types.
+export const entry = t.union([
+  entriesMatch,
+  entriesMatchAny,
+  entriesList,
+  entriesExists,
+  entriesMatchWildcard,
+]);
 export type Entry = t.TypeOf<typeof entry>;
 
 export const entriesArray = t.array(
-  t.union([entriesMatch, entriesMatchAny, entriesList, entriesExists, entriesNested])
+  t.union([
+    entriesMatch,
+    entriesMatchAny,
+    entriesList,
+    entriesExists,
+    entriesNested,
+    entriesMatchWildcard,
+  ])
 );
 export type EntriesArray = t.TypeOf<typeof entriesArray>;
 
diff --git a/x-pack/plugins/lists/common/schemas/types/entry_match_wildcard.mock.ts b/x-pack/plugins/lists/common/schemas/types/entry_match_wildcard.mock.ts
new file mode 100644
index 0000000000000..3204bbe064496
--- /dev/null
+++ b/x-pack/plugins/lists/common/schemas/types/entry_match_wildcard.mock.ts
@@ -0,0 +1,22 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import { ENTRY_VALUE, FIELD, OPERATOR, WILDCARD } from '../../constants.mock';
+
+import { EntryMatchWildcard } from './entry_match_wildcard';
+
+export const getEntryMatchWildcardMock = (): EntryMatchWildcard => ({
+  field: FIELD,
+  operator: OPERATOR,
+  type: WILDCARD,
+  value: ENTRY_VALUE,
+});
+
+export const getEntryMatchWildcardExcludeMock = (): EntryMatchWildcard => ({
+  ...getEntryMatchWildcardMock(),
+  operator: 'excluded',
+});
diff --git a/x-pack/plugins/lists/common/schemas/types/entry_match_wildcard.test.ts b/x-pack/plugins/lists/common/schemas/types/entry_match_wildcard.test.ts
new file mode 100644
index 0000000000000..53cfc4fdff1f5
--- /dev/null
+++ b/x-pack/plugins/lists/common/schemas/types/entry_match_wildcard.test.ts
@@ -0,0 +1,106 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import { pipe } from 'fp-ts/lib/pipeable';
+import { left } from 'fp-ts/lib/Either';
+
+import { foldLeftRight, getPaths } from '../../shared_imports';
+
+import { getEntryMatchWildcardMock } from './entry_match_wildcard.mock';
+import { EntryMatchWildcard, entriesMatchWildcard } from './entry_match_wildcard';
+
+describe('entriesMatchWildcard', () => {
+  test('it should validate an entry', () => {
+    const payload = getEntryMatchWildcardMock();
+    const decoded = entriesMatchWildcard.decode(payload);
+    const message = pipe(decoded, foldLeftRight);
+
+    expect(getPaths(left(message.errors))).toEqual([]);
+    expect(message.schema).toEqual(payload);
+  });
+
+  test('it should validate when operator is "included"', () => {
+    const payload = getEntryMatchWildcardMock();
+    const decoded = entriesMatchWildcard.decode(payload);
+    const message = pipe(decoded, foldLeftRight);
+
+    expect(getPaths(left(message.errors))).toEqual([]);
+    expect(message.schema).toEqual(payload);
+  });
+
+  test('it should validate when "operator" is "excluded"', () => {
+    const payload = getEntryMatchWildcardMock();
+    payload.operator = 'excluded';
+    const decoded = entriesMatchWildcard.decode(payload);
+    const message = pipe(decoded, foldLeftRight);
+
+    expect(getPaths(left(message.errors))).toEqual([]);
+    expect(message.schema).toEqual(payload);
+  });
+
+  test('it should FAIL validation when "field" is empty string', () => {
+    const payload: Omit<EntryMatchWildcard, 'field'> & { field: string } = {
+      ...getEntryMatchWildcardMock(),
+      field: '',
+    };
+    const decoded = entriesMatchWildcard.decode(payload);
+    const message = pipe(decoded, foldLeftRight);
+
+    expect(getPaths(left(message.errors))).toEqual(['Invalid value "" supplied to "field"']);
+    expect(message.schema).toEqual({});
+  });
+
+  test('it should FAIL validation when "value" is not string', () => {
+    const payload: Omit<EntryMatchWildcard, 'value'> & { value: string[] } = {
+      ...getEntryMatchWildcardMock(),
+      value: ['some value'],
+    };
+    const decoded = entriesMatchWildcard.decode(payload);
+    const message = pipe(decoded, foldLeftRight);
+
+    expect(getPaths(left(message.errors))).toEqual([
+      'Invalid value "["some value"]" supplied to "value"',
+    ]);
+    expect(message.schema).toEqual({});
+  });
+
+  test('it should FAIL validation when "value" is empty string', () => {
+    const payload: Omit<EntryMatchWildcard, 'value'> & { value: string } = {
+      ...getEntryMatchWildcardMock(),
+      value: '',
+    };
+    const decoded = entriesMatchWildcard.decode(payload);
+    const message = pipe(decoded, foldLeftRight);
+
+    expect(getPaths(left(message.errors))).toEqual(['Invalid value "" supplied to "value"']);
+    expect(message.schema).toEqual({});
+  });
+
+  test('it should FAIL validation when "type" is not "wildcard"', () => {
+    const payload: Omit<EntryMatchWildcard, 'type'> & { type: string } = {
+      ...getEntryMatchWildcardMock(),
+      type: 'match',
+    };
+    const decoded = entriesMatchWildcard.decode(payload);
+    const message = pipe(decoded, foldLeftRight);
+
+    expect(getPaths(left(message.errors))).toEqual(['Invalid value "match" supplied to "type"']);
+    expect(message.schema).toEqual({});
+  });
+
+  test('it should strip out extra keys', () => {
+    const payload: EntryMatchWildcard & {
+      extraKey?: string;
+    } = getEntryMatchWildcardMock();
+    payload.extraKey = 'some value';
+    const decoded = entriesMatchWildcard.decode(payload);
+    const message = pipe(decoded, foldLeftRight);
+
+    expect(getPaths(left(message.errors))).toEqual([]);
+    expect(message.schema).toEqual(getEntryMatchWildcardMock());
+  });
+});
diff --git a/x-pack/plugins/lists/common/schemas/types/entry_match_wildcard.ts b/x-pack/plugins/lists/common/schemas/types/entry_match_wildcard.ts
new file mode 100644
index 0000000000000..14522256df354
--- /dev/null
+++ b/x-pack/plugins/lists/common/schemas/types/entry_match_wildcard.ts
@@ -0,0 +1,21 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import * as t from 'io-ts';
+
+import { NonEmptyString } from '../../shared_imports';
+import { operator } from '../common/schemas';
+
+export const entriesMatchWildcard = t.exact(
+  t.type({
+    field: NonEmptyString,
+    operator,
+    type: t.keyof({ wildcard: null }),
+    value: NonEmptyString,
+  })
+);
+export type EntryMatchWildcard = t.TypeOf<typeof entriesMatchWildcard>;
diff --git a/x-pack/plugins/lists/common/schemas/types/index.ts b/x-pack/plugins/lists/common/schemas/types/index.ts
index 98342f3b9c153..ebe21174570cb 100644
--- a/x-pack/plugins/lists/common/schemas/types/index.ts
+++ b/x-pack/plugins/lists/common/schemas/types/index.ts
@@ -15,6 +15,7 @@ export * from './default_namespace';
 export * from './entries';
 export * from './entry_match';
 export * from './entry_match_any';
+export * from './entry_match_wildcard';
 export * from './entry_list';
 export * from './entry_exists';
 export * from './entry_nested';
diff --git a/x-pack/plugins/lists/common/shared_exports.ts b/x-pack/plugins/lists/common/shared_exports.ts
index 286fee6de5425..8be53cb8cddbc 100644
--- a/x-pack/plugins/lists/common/shared_exports.ts
+++ b/x-pack/plugins/lists/common/shared_exports.ts
@@ -20,6 +20,7 @@ export {
   EntryExists,
   EntryMatch,
   EntryMatchAny,
+  EntryMatchWildcard,
   EntryNested,
   EntryList,
   EntriesArray,
@@ -39,6 +40,7 @@ export {
   nestedEntryItem,
   entriesMatch,
   entriesMatchAny,
+  entriesMatchWildcard,
   entriesExists,
   entriesList,
   namespaceType,
diff --git a/x-pack/plugins/lists/public/exceptions/components/builder/types.ts b/x-pack/plugins/lists/public/exceptions/components/builder/types.ts
index cdb4f735aa103..800f1445217b9 100644
--- a/x-pack/plugins/lists/public/exceptions/components/builder/types.ts
+++ b/x-pack/plugins/lists/public/exceptions/components/builder/types.ts
@@ -13,6 +13,7 @@ import {
   EntryExists,
   EntryMatch,
   EntryMatchAny,
+  EntryMatchWildcard,
   EntryNested,
   ExceptionListItemSchema,
   OperatorEnum,
@@ -34,7 +35,7 @@ export interface EmptyEntry {
   id: string;
   field: string | undefined;
   operator: OperatorEnum;
-  type: OperatorTypeEnum.MATCH | OperatorTypeEnum.MATCH_ANY;
+  type: OperatorTypeEnum.MATCH | OperatorTypeEnum.MATCH_ANY | OperatorTypeEnum.WILDCARD;
   value: string | string[] | undefined;
 }
 
@@ -53,6 +54,7 @@ export interface EmptyNestedEntry {
   entries: Array<
     | (EntryMatch & { id?: string })
     | (EntryMatchAny & { id?: string })
+    | (EntryMatchWildcard & { id?: string })
     | (EntryExists & { id?: string })
   >;
 }
@@ -69,6 +71,7 @@ export type BuilderEntryNested = Omit<EntryNested, 'entries'> & {
   entries: Array<
     | (EntryMatch & { id?: string })
     | (EntryMatchAny & { id?: string })
+    | (EntryMatchWildcard & { id?: string })
     | (EntryExists & { id?: string })
   >;
 };
diff --git a/x-pack/plugins/security_solution/common/endpoint/schema/trusted_apps.test.ts b/x-pack/plugins/security_solution/common/endpoint/schema/trusted_apps.test.ts
index 326795ae55662..df0d0d7acf4c7 100644
--- a/x-pack/plugins/security_solution/common/endpoint/schema/trusted_apps.test.ts
+++ b/x-pack/plugins/security_solution/common/endpoint/schema/trusted_apps.test.ts
@@ -247,6 +247,30 @@ describe('When invoking Trusted Apps Schema', () => {
         expect(() => body.validate(bodyMsg)).not.toThrow();
       });
 
+      it('should validate `entry.type` does not accept `wildcard` when field is NOT PATH', () => {
+        const bodyMsg = createNewTrustedApp({
+          entries: [
+            createConditionEntry({
+              field: ConditionEntryField.HASH,
+              type: 'wildcard',
+            }),
+          ],
+        });
+        expect(() => body.validate(bodyMsg)).toThrow();
+      });
+
+      it('should validate `entry.type` accepts `wildcard` when field is PATH', () => {
+        const bodyMsg = createNewTrustedApp({
+          entries: [
+            createConditionEntry({
+              field: ConditionEntryField.PATH,
+              type: 'wildcard',
+            }),
+          ],
+        });
+        expect(() => body.validate(bodyMsg)).not.toThrow();
+      });
+
       it('should validate `entry.value` required', () => {
         const { value, ...entry } = createConditionEntry();
         expect(() => body.validate(createNewTrustedApp({ entries: [entry] }))).toThrow();
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 e582744e1a141..54d0becd2446e 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
@@ -29,7 +29,12 @@ export const GetTrustedAppsRequestSchema = {
   }),
 };
 
-const ConditionEntryTypeSchema = schema.literal('match');
+const ConditionEntryTypeSchema = schema.conditional(
+  schema.siblingRef('field'),
+  ConditionEntryField.PATH,
+  schema.oneOf([schema.literal('match'), schema.literal('wildcard')]),
+  schema.literal('match')
+);
 const ConditionEntryOperatorSchema = schema.literal('included');
 
 /*
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 d36958c11d2a1..8d66370fea4d3 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 +7,7 @@
 
 import { TypeOf } from '@kbn/config-schema';
 import { ApplicationStart } from 'kibana/public';
+
 import {
   DeleteTrustedAppsRequestSchema,
   GetOneTrustedAppRequestSchema,
@@ -69,9 +70,15 @@ export enum ConditionEntryField {
   SIGNER = 'process.Ext.code_signature',
 }
 
+export enum OperatorFieldIds {
+  is = 'is',
+  matches = 'matches',
+}
+
+export type TrustedAppEntryTypes = 'match' | 'wildcard';
 export interface ConditionEntry<T extends ConditionEntryField = ConditionEntryField> {
   field: T;
-  type: 'match';
+  type: TrustedAppEntryTypes;
   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 033df0df6c458..e987775a8e768 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,
+  EntryMatchWildcard,
   EntryNested,
   EntryList,
   EntriesArray,
@@ -38,6 +39,7 @@ export {
   nestedEntryItem,
   entriesMatch,
   entriesMatchAny,
+  entriesMatchWildcard,
   entriesExists,
   entriesList,
   namespaceType,
diff --git a/x-pack/plugins/security_solution/common/utils/path_placeholder.test.ts b/x-pack/plugins/security_solution/common/utils/path_placeholder.test.ts
new file mode 100644
index 0000000000000..9618440c105dc
--- /dev/null
+++ b/x-pack/plugins/security_solution/common/utils/path_placeholder.test.ts
@@ -0,0 +1,69 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import { getPlaceholderTextByOSType, getPlaceholderText } from './path_placeholder';
+import { ConditionEntryField, OperatingSystem, TrustedAppEntryTypes } from '../endpoint/types';
+
+const trustedAppEntry = {
+  os: OperatingSystem.LINUX,
+  field: ConditionEntryField.HASH,
+  type: 'match' as TrustedAppEntryTypes,
+};
+
+describe('Trusted Apps: Path placeholder text', () => {
+  it('returns no placeholder text when field IS NOT PATH', () => {
+    expect(getPlaceholderTextByOSType({ ...trustedAppEntry })).toEqual(undefined);
+  });
+
+  it('returns a placeholder text when field IS PATH', () => {
+    expect(
+      getPlaceholderTextByOSType({ ...trustedAppEntry, field: ConditionEntryField.PATH })
+    ).toEqual(getPlaceholderText().others.exact);
+  });
+
+  it('returns LINUX/MAC equivalent placeholder when field IS PATH', () => {
+    expect(
+      getPlaceholderTextByOSType({
+        ...trustedAppEntry,
+        os: OperatingSystem.MAC,
+        field: ConditionEntryField.PATH,
+      })
+    ).toEqual(getPlaceholderText().others.exact);
+  });
+
+  it('returns LINUX/MAC equivalent placeholder text when field IS PATH and WILDCARD operator is selected', () => {
+    expect(
+      getPlaceholderTextByOSType({
+        ...trustedAppEntry,
+        os: OperatingSystem.LINUX,
+        field: ConditionEntryField.PATH,
+        type: 'wildcard',
+      })
+    ).toEqual(getPlaceholderText().others.wildcard);
+  });
+
+  it('returns WINDOWS equivalent placeholder text when field IS PATH', () => {
+    expect(
+      getPlaceholderTextByOSType({
+        ...trustedAppEntry,
+        os: OperatingSystem.WINDOWS,
+        field: ConditionEntryField.PATH,
+      })
+    ).toEqual(getPlaceholderText().windows.exact);
+  });
+
+  it('returns WINDOWS equivalent placeholder text when field IS PATH and WILDCARD operator is selected', () => {
+    expect(
+      getPlaceholderTextByOSType({
+        ...trustedAppEntry,
+        os: OperatingSystem.WINDOWS,
+        field: ConditionEntryField.PATH,
+        type: 'wildcard',
+      })
+    ).toEqual(getPlaceholderText().windows.wildcard);
+  });
+});
diff --git a/x-pack/plugins/security_solution/common/utils/path_placeholder.ts b/x-pack/plugins/security_solution/common/utils/path_placeholder.ts
new file mode 100644
index 0000000000000..bba01b6d05b65
--- /dev/null
+++ b/x-pack/plugins/security_solution/common/utils/path_placeholder.ts
@@ -0,0 +1,43 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import { ConditionEntryField, OperatingSystem, TrustedAppEntryTypes } from '../endpoint/types';
+
+export const getPlaceholderText = () => ({
+  windows: {
+    wildcard: 'C:\\sample\\**\\*',
+    exact: 'C:\\sample\\path.exe',
+  },
+  others: {
+    wildcard: '/opt/**/*',
+    exact: '/opt/bin',
+  },
+});
+
+export const getPlaceholderTextByOSType = ({
+  os,
+  field,
+  type,
+}: {
+  os: OperatingSystem;
+  field: ConditionEntryField;
+  type: TrustedAppEntryTypes;
+}): string | undefined => {
+  if (field === ConditionEntryField.PATH) {
+    if (os === OperatingSystem.WINDOWS) {
+      if (type === 'wildcard') {
+        return getPlaceholderText().windows.wildcard;
+      }
+      return getPlaceholderText().windows.exact;
+    } else {
+      if (type === 'wildcard') {
+        return getPlaceholderText().others.wildcard;
+      }
+      return getPlaceholderText().others.exact;
+    }
+  }
+};
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..92a3cb2cfac93 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,
+  EntryMatchWildcard,
   EntryExists,
   ExceptionListItemSchema,
   CreateExceptionListItemSchema,
@@ -92,6 +93,7 @@ export interface EmptyNestedEntry {
   type: OperatorTypeEnum.NESTED;
   entries: Array<
     | (EntryMatch & { id?: string })
+    | (EntryMatchWildcard & { 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 })
+    | (EntryMatchWildcard & { 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.test.tsx b/x-pack/plugins/security_solution/public/management/pages/trusted_apps/view/components/condition_entry_input/index.test.tsx
index 4e9ec3a0883a2..9d6c35d64b2d5 100644
--- a/x-pack/plugins/security_solution/public/management/pages/trusted_apps/view/components/condition_entry_input/index.test.tsx
+++ b/x-pack/plugins/security_solution/public/management/pages/trusted_apps/view/components/condition_entry_input/index.test.tsx
@@ -21,7 +21,7 @@ let onRemoveMock: jest.Mock;
 let onChangeMock: jest.Mock;
 let onVisitedMock: jest.Mock;
 
-const entry: Readonly<ConditionEntry> = {
+const baseEntry: Readonly<ConditionEntry> = {
   field: ConditionEntryField.HASH,
   type: 'match',
   operator: 'included',
@@ -38,7 +38,8 @@ describe('Condition entry input', () => {
   const getElement = (
     subject: string,
     os: OperatingSystem = OperatingSystem.WINDOWS,
-    isRemoveDisabled: boolean = false
+    isRemoveDisabled: boolean = false,
+    entry: ConditionEntry = baseEntry
   ) => (
     <ConditionEntryInput
       os={os}
@@ -64,10 +65,10 @@ describe('Condition entry input', () => {
       expect(onChangeMock).toHaveBeenCalledTimes(1);
       expect(onChangeMock).toHaveBeenCalledWith(
         {
-          ...entry,
+          ...baseEntry,
           field: { target: { value: field } },
         },
-        entry
+        baseEntry
       );
     }
   );
@@ -77,7 +78,7 @@ describe('Condition entry input', () => {
     expect(onRemoveMock).toHaveBeenCalledTimes(0);
     element.find('[data-test-subj="testOnRemove-remove"]').first().simulate('click');
     expect(onRemoveMock).toHaveBeenCalledTimes(1);
-    expect(onRemoveMock).toHaveBeenCalledWith(entry);
+    expect(onRemoveMock).toHaveBeenCalledWith(baseEntry);
   });
 
   it('should not be able to call on remove for field input because disabled', () => {
@@ -92,7 +93,7 @@ describe('Condition entry input', () => {
     expect(onVisitedMock).toHaveBeenCalledTimes(0);
     element.find('[data-test-subj="testOnVisited-value"]').first().simulate('blur');
     expect(onVisitedMock).toHaveBeenCalledTimes(1);
-    expect(onVisitedMock).toHaveBeenCalledWith(entry);
+    expect(onVisitedMock).toHaveBeenCalledWith(baseEntry);
   });
 
   it('should change value for field input', () => {
@@ -105,10 +106,10 @@ describe('Condition entry input', () => {
     expect(onChangeMock).toHaveBeenCalledTimes(1);
     expect(onChangeMock).toHaveBeenCalledWith(
       {
-        ...entry,
+        ...baseEntry,
         value: 'new value',
       },
-      entry
+      baseEntry
     );
   });
 
@@ -138,4 +139,24 @@ describe('Condition entry input', () => {
       .props() as EuiSuperSelectProps<string>;
     expect(superSelectProps.options.length).toBe(2);
   });
+
+  it('should have operator value selected when field is HASH', () => {
+    const element = shallow(getElement('testOperatorOptions'));
+    const inputField = element.find('[data-test-subj="testOperatorOptions-operator"]');
+    expect(inputField.contains('is'));
+  });
+
+  it('should show operator dorpdown with two values when field is PATH', () => {
+    const element = shallow(
+      getElement('testOperatorOptions', undefined, undefined, {
+        ...baseEntry,
+        field: ConditionEntryField.PATH,
+      })
+    );
+    const superSelectProps = element
+      .find('[data-test-subj="testOperatorOptions-operator"]')
+      .first()
+      .props() as EuiSuperSelectProps<string>;
+    expect(superSelectProps.options.length).toBe(2);
+  });
 });
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 633adde4fdfbb..d052138d309ac 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
@@ -6,12 +6,11 @@
  */
 
 import React, { ChangeEventHandler, memo, useCallback, useMemo } from 'react';
+import styled from 'styled-components';
 import { i18n } from '@kbn/i18n';
 import {
   EuiButtonIcon,
   EuiFieldText,
-  EuiFlexGroup,
-  EuiFlexItem,
   EuiFormRow,
   EuiSuperSelect,
   EuiSuperSelectOption,
@@ -21,6 +20,7 @@ import {
 import {
   ConditionEntry,
   ConditionEntryField,
+  OperatorFieldIds,
   OperatingSystem,
 } from '../../../../../../../common/endpoint/types';
 
@@ -28,9 +28,10 @@ import {
   CONDITION_FIELD_DESCRIPTION,
   CONDITION_FIELD_TITLE,
   ENTRY_PROPERTY_TITLES,
-  OPERATOR_TITLE,
+  OPERATOR_TITLES,
 } from '../../translations';
 import { useTestIdGenerator } from '../../../../../components/hooks/use_test_id_generator';
+import { getPlaceholderTextByOSType } from '../../../../../../../common/utils/path_placeholder';
 
 const ConditionEntryCell = memo<{
   showLabel: boolean;
@@ -66,6 +67,27 @@ export interface ConditionEntryInputProps {
   'data-test-subj'?: string;
 }
 
+// adding a style prop on EuiFlexGroup works only partially
+// and for some odd reason garbles up gridTemplateAreas entry
+const InputGroup = styled.div`
+  display: grid;
+  grid-template-columns: 25% 25% 45% 5%;
+  grid-template-areas: 'field operator value remove';
+`;
+
+const InputItem = styled.div<{ gridArea: string }>`
+  grid-area: ${({ gridArea }) => gridArea};
+  align-self: center;
+  margin: 4px;
+  vertical-align: baseline;
+`;
+
+const operatorOptions = (Object.keys(OperatorFieldIds) as OperatorFieldIds[]).map((value) => ({
+  dropdownDisplay: OPERATOR_TITLES[value],
+  inputDisplay: OPERATOR_TITLES[value],
+  value: value === 'matches' ? 'wildcard' : 'match',
+}));
+
 export const ConditionEntryInput = memo<ConditionEntryInputProps>(
   ({
     os,
@@ -122,6 +144,11 @@ export const ConditionEntryInput = memo<ConditionEntryInputProps>(
       [entry, onChange]
     );
 
+    const handleOperatorUpdate = useCallback(
+      (newOperator) => onChange({ ...entry, type: newOperator }, entry),
+      [entry, onChange]
+    );
+
     const handleRemoveClick = useCallback(() => onRemove(entry), [entry, onRemove]);
 
     const handleValueOnBlur = useCallback(() => {
@@ -131,14 +158,8 @@ export const ConditionEntryInput = memo<ConditionEntryInputProps>(
     }, [entry, onVisited]);
 
     return (
-      <EuiFlexGroup
-        gutterSize="s"
-        alignItems="center"
-        direction="row"
-        data-test-subj={dataTestSubj}
-        responsive={false}
-      >
-        <EuiFlexItem grow={2}>
+      <InputGroup data-test-subj={dataTestSubj}>
+        <InputItem gridArea="field">
           <ConditionEntryCell showLabel={showLabels} label={ENTRY_PROPERTY_TITLES.field}>
             <EuiSuperSelect
               options={fieldOptions}
@@ -147,17 +168,36 @@ export const ConditionEntryInput = memo<ConditionEntryInputProps>(
               data-test-subj={getTestId('field')}
             />
           </ConditionEntryCell>
-        </EuiFlexItem>
-        <EuiFlexItem>
+        </InputItem>
+        <InputItem gridArea="operator">
           <ConditionEntryCell showLabel={showLabels} label={ENTRY_PROPERTY_TITLES.operator}>
-            <EuiFieldText name="operator" value={OPERATOR_TITLE.included} readOnly />
+            {entry.field === ConditionEntryField.PATH ? (
+              <EuiSuperSelect
+                options={operatorOptions}
+                onChange={handleOperatorUpdate}
+                valueOfSelected={entry.type}
+                data-test-subj={getTestId('operator')}
+              />
+            ) : (
+              <EuiFieldText
+                name="operator"
+                value={OPERATOR_TITLES.is}
+                data-test-subj={getTestId('operator')}
+                readOnly
+              />
+            )}
           </ConditionEntryCell>
-        </EuiFlexItem>
-        <EuiFlexItem grow={3}>
+        </InputItem>
+        <InputItem gridArea="value">
           <ConditionEntryCell showLabel={showLabels} label={ENTRY_PROPERTY_TITLES.value}>
             <EuiFieldText
               name="value"
               value={entry.value}
+              placeholder={getPlaceholderTextByOSType({
+                os,
+                field: entry.field,
+                type: entry.type,
+              })}
               fullWidth
               required
               onChange={handleValueUpdate}
@@ -165,8 +205,8 @@ export const ConditionEntryInput = memo<ConditionEntryInputProps>(
               data-test-subj={getTestId('value')}
             />
           </ConditionEntryCell>
-        </EuiFlexItem>
-        <EuiFlexItem grow={false}>
+        </InputItem>
+        <InputItem gridArea="remove">
           {/* Unicode `nbsp` is used below so that Remove button is property displayed */}
           <ConditionEntryCell showLabel={showLabels} label={'\u00A0'}>
             <EuiButtonIcon
@@ -181,8 +221,8 @@ export const ConditionEntryInput = memo<ConditionEntryInputProps>(
               data-test-subj={getTestId('remove')}
             />
           </ConditionEntryCell>
-        </EuiFlexItem>
-      </EuiFlexGroup>
+        </InputItem>
+      </InputGroup>
     );
   }
 );
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 0520f760d7343..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
@@ -31,7 +31,7 @@ import {
   ENTRY_PROPERTY_TITLES,
   CARD_DELETE_BUTTON_LABEL,
   CONDITION_FIELD_TITLE,
-  OPERATOR_TITLE,
+  OPERATOR_TITLES,
   CARD_EDIT_BUTTON_LABEL,
 } from '../../translations';
 
@@ -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_TITLE[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 c3e2a372fd6dc..fc031a63b84b1 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
@@ -10,8 +10,8 @@ import {
   TrustedApp,
   MacosLinuxConditionEntry,
   WindowsConditionEntry,
-  ConditionEntry,
   ConditionEntryField,
+  OperatorFieldIds,
 } from '../../../../../common/endpoint/types';
 
 export { OS_TITLES } from '../../../common/translations';
@@ -52,10 +52,13 @@ export const CONDITION_FIELD_DESCRIPTION: { [K in ConditionEntryField]: string }
   ),
 };
 
-export const OPERATOR_TITLE: { [K in ConditionEntry['operator']]: string } = {
-  included: i18n.translate('xpack.securitySolution.trustedapps.card.operator.includes', {
+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/lib/artifacts/lists.ts b/x-pack/plugins/security_solution/server/endpoint/lib/artifacts/lists.ts
index 1c3c92c50afd3..54b6971eec58e 100644
--- a/x-pack/plugins/security_solution/server/endpoint/lib/artifacts/lists.ts
+++ b/x-pack/plugins/security_solution/server/endpoint/lib/artifacts/lists.ts
@@ -22,6 +22,8 @@ import {
   translatedEntryMatchAnyMatcher,
   TranslatedEntryMatcher,
   translatedEntryMatchMatcher,
+  TranslatedEntryMatchWildcardMatcher,
+  translatedEntryMatchWildcardMatcher,
   TranslatedEntryNestedEntry,
   translatedEntryNestedEntry,
   TranslatedExceptionListItem,
@@ -203,6 +205,10 @@ function getMatcherFunction(field: string, matchAny?: boolean): TranslatedEntryM
     : 'exact_cased';
 }
 
+function getMatcherWildcardFunction(field: string): TranslatedEntryMatchWildcardMatcher {
+  return field.endsWith('.caseless') ? 'wildcard_caseless' : 'wildcard_cased';
+}
+
 function normalizeFieldName(field: string): string {
   return field.endsWith('.caseless') ? field.substring(0, field.lastIndexOf('.')) : field;
 }
@@ -272,6 +278,17 @@ function translateEntry(
           }
         : undefined;
     }
+    case 'wildcard': {
+      const matcher = getMatcherWildcardFunction(entry.field);
+      return translatedEntryMatchWildcardMatcher.is(matcher)
+        ? {
+            field: normalizeFieldName(entry.field),
+            operator: entry.operator,
+            type: matcher,
+            value: entry.value,
+          }
+        : undefined;
+    }
   }
 }
 
diff --git a/x-pack/plugins/security_solution/server/endpoint/routes/trusted_apps/handlers.test.ts b/x-pack/plugins/security_solution/server/endpoint/routes/trusted_apps/handlers.test.ts
index 42a2e0f43d970..0b4e1cb2b09b1 100644
--- a/x-pack/plugins/security_solution/server/endpoint/routes/trusted_apps/handlers.test.ts
+++ b/x-pack/plugins/security_solution/server/endpoint/routes/trusted_apps/handlers.test.ts
@@ -66,8 +66,8 @@ const NEW_TRUSTED_APP: NewTrustedApp = {
   os: OperatingSystem.LINUX,
   effectScope: { type: 'global' },
   entries: [
-    createConditionEntry(ConditionEntryField.PATH, '/bin/malware'),
-    createConditionEntry(ConditionEntryField.HASH, '1234234659af249ddf3e40864e9fb241'),
+    createConditionEntry(ConditionEntryField.PATH, 'match', '/bin/malware'),
+    createConditionEntry(ConditionEntryField.HASH, 'match', '1234234659af249ddf3e40864e9fb241'),
   ],
 };
 
@@ -83,8 +83,8 @@ const TRUSTED_APP: TrustedApp = {
   os: OperatingSystem.LINUX,
   effectScope: { type: 'global' },
   entries: [
-    createConditionEntry(ConditionEntryField.HASH, '1234234659af249ddf3e40864e9fb241'),
-    createConditionEntry(ConditionEntryField.PATH, '/bin/malware'),
+    createConditionEntry(ConditionEntryField.HASH, 'match', '1234234659af249ddf3e40864e9fb241'),
+    createConditionEntry(ConditionEntryField.PATH, 'match', '/bin/malware'),
   ],
 };
 
diff --git a/x-pack/plugins/security_solution/server/endpoint/routes/trusted_apps/mapping.test.ts b/x-pack/plugins/security_solution/server/endpoint/routes/trusted_apps/mapping.test.ts
index 68ff7d03e413a..9ee2ece627841 100644
--- a/x-pack/plugins/security_solution/server/endpoint/routes/trusted_apps/mapping.test.ts
+++ b/x-pack/plugins/security_solution/server/endpoint/routes/trusted_apps/mapping.test.ts
@@ -79,13 +79,19 @@ describe('mapping', () => {
           description: 'Linux Trusted App',
           effectScope: { type: 'global' },
           os: OperatingSystem.LINUX,
-          entries: [createConditionEntry(ConditionEntryField.PATH, '/bin/malware')],
+          entries: [createConditionEntry(ConditionEntryField.PATH, 'match', '/bin/malware')],
         },
         createExceptionListItemOptions({
           name: 'linux trusted app',
           description: 'Linux Trusted App',
           osTypes: ['linux'],
-          entries: [createEntryMatch('process.executable.caseless', '/bin/malware')],
+          entries: [
+            createEntryMatch(
+              'process.executable.caseless',
+
+              '/bin/malware'
+            ),
+          ],
         })
       );
     });
@@ -97,13 +103,19 @@ describe('mapping', () => {
           description: 'MacOS Trusted App',
           effectScope: { type: 'global' },
           os: OperatingSystem.MAC,
-          entries: [createConditionEntry(ConditionEntryField.PATH, '/bin/malware')],
+          entries: [createConditionEntry(ConditionEntryField.PATH, 'match', '/bin/malware')],
         },
         createExceptionListItemOptions({
           name: 'macos trusted app',
           description: 'MacOS Trusted App',
           osTypes: ['macos'],
-          entries: [createEntryMatch('process.executable.caseless', '/bin/malware')],
+          entries: [
+            createEntryMatch(
+              'process.executable.caseless',
+
+              '/bin/malware'
+            ),
+          ],
         })
       );
     });
@@ -115,13 +127,21 @@ describe('mapping', () => {
           description: 'Windows Trusted App',
           effectScope: { type: 'global' },
           os: OperatingSystem.WINDOWS,
-          entries: [createConditionEntry(ConditionEntryField.PATH, 'C:\\Program Files\\Malware')],
+          entries: [
+            createConditionEntry(ConditionEntryField.PATH, 'match', 'C:\\Program Files\\Malware'),
+          ],
         },
         createExceptionListItemOptions({
           name: 'windows trusted app',
           description: 'Windows Trusted App',
           osTypes: ['windows'],
-          entries: [createEntryMatch('process.executable.caseless', 'C:\\Program Files\\Malware')],
+          entries: [
+            createEntryMatch(
+              'process.executable.caseless',
+
+              'C:\\Program Files\\Malware'
+            ),
+          ],
         })
       );
     });
@@ -133,7 +153,7 @@ describe('mapping', () => {
           description: 'Signed Trusted App',
           effectScope: { type: 'global' },
           os: OperatingSystem.WINDOWS,
-          entries: [createConditionEntry(ConditionEntryField.SIGNER, 'Microsoft Windows')],
+          entries: [createConditionEntry(ConditionEntryField.SIGNER, 'match', 'Microsoft Windows')],
         },
         createExceptionListItemOptions({
           name: 'Signed trusted app',
@@ -157,14 +177,24 @@ describe('mapping', () => {
           effectScope: { type: 'global' },
           os: OperatingSystem.LINUX,
           entries: [
-            createConditionEntry(ConditionEntryField.HASH, '1234234659af249ddf3e40864e9fb241'),
+            createConditionEntry(
+              ConditionEntryField.HASH,
+              'match',
+              '1234234659af249ddf3e40864e9fb241'
+            ),
           ],
         },
         createExceptionListItemOptions({
           name: 'MD5 trusted app',
           description: 'MD5 Trusted App',
           osTypes: ['linux'],
-          entries: [createEntryMatch('process.hash.md5', '1234234659af249ddf3e40864e9fb241')],
+          entries: [
+            createEntryMatch(
+              'process.hash.md5',
+
+              '1234234659af249ddf3e40864e9fb241'
+            ),
+          ],
         })
       );
     });
@@ -179,6 +209,7 @@ describe('mapping', () => {
           entries: [
             createConditionEntry(
               ConditionEntryField.HASH,
+              'match',
               'f635da961234234659af249ddf3e40864e9fb241'
             ),
           ],
@@ -188,7 +219,11 @@ describe('mapping', () => {
           description: 'SHA1 Trusted App',
           osTypes: ['linux'],
           entries: [
-            createEntryMatch('process.hash.sha1', 'f635da961234234659af249ddf3e40864e9fb241'),
+            createEntryMatch(
+              'process.hash.sha1',
+
+              'f635da961234234659af249ddf3e40864e9fb241'
+            ),
           ],
         })
       );
@@ -204,6 +239,7 @@ describe('mapping', () => {
           entries: [
             createConditionEntry(
               ConditionEntryField.HASH,
+              'match',
               'f635da96124659af249ddf3e40864e9fb234234659af249ddf3e40864e9fb241'
             ),
           ],
@@ -215,6 +251,7 @@ describe('mapping', () => {
           entries: [
             createEntryMatch(
               'process.hash.sha256',
+
               'f635da96124659af249ddf3e40864e9fb234234659af249ddf3e40864e9fb241'
             ),
           ],
@@ -230,14 +267,24 @@ describe('mapping', () => {
           effectScope: { type: 'global' },
           os: OperatingSystem.LINUX,
           entries: [
-            createConditionEntry(ConditionEntryField.HASH, '1234234659Af249ddf3e40864E9FB241'),
+            createConditionEntry(
+              ConditionEntryField.HASH,
+              'match',
+              '1234234659Af249ddf3e40864E9FB241'
+            ),
           ],
         },
         createExceptionListItemOptions({
           name: 'MD5 trusted app',
           description: 'MD5 Trusted App',
           osTypes: ['linux'],
-          entries: [createEntryMatch('process.hash.md5', '1234234659af249ddf3e40864e9fb241')],
+          entries: [
+            createEntryMatch(
+              'process.hash.md5',
+
+              '1234234659af249ddf3e40864e9fb241'
+            ),
+          ],
         })
       );
     });
@@ -257,7 +304,13 @@ describe('mapping', () => {
           created_at: '11/11/2011T11:11:11.111',
           created_by: 'admin',
           os_types: ['linux'],
-          entries: [createEntryMatch('process.executable.caseless', '/bin/malware')],
+          entries: [
+            createEntryMatch(
+              'process.executable.caseless',
+
+              '/bin/malware'
+            ),
+          ],
         }),
         {
           id: '123',
@@ -270,7 +323,7 @@ describe('mapping', () => {
           updated_at: '11/11/2011T11:11:11.111',
           updated_by: 'admin',
           os: OperatingSystem.LINUX,
-          entries: [createConditionEntry(ConditionEntryField.PATH, '/bin/malware')],
+          entries: [createConditionEntry(ConditionEntryField.PATH, 'match', '/bin/malware')],
         }
       );
     });
@@ -284,7 +337,13 @@ describe('mapping', () => {
           created_at: '11/11/2011T11:11:11.111',
           created_by: 'admin',
           os_types: ['macos'],
-          entries: [createEntryMatch('process.executable.caseless', '/bin/malware')],
+          entries: [
+            createEntryMatch(
+              'process.executable.caseless',
+
+              '/bin/malware'
+            ),
+          ],
         }),
         {
           id: '123',
@@ -297,7 +356,7 @@ describe('mapping', () => {
           updated_at: '11/11/2011T11:11:11.111',
           updated_by: 'admin',
           os: OperatingSystem.MAC,
-          entries: [createConditionEntry(ConditionEntryField.PATH, '/bin/malware')],
+          entries: [createConditionEntry(ConditionEntryField.PATH, 'match', '/bin/malware')],
         }
       );
     });
@@ -311,7 +370,13 @@ describe('mapping', () => {
           created_at: '11/11/2011T11:11:11.111',
           created_by: 'admin',
           os_types: ['windows'],
-          entries: [createEntryMatch('process.executable.caseless', 'C:\\Program Files\\Malware')],
+          entries: [
+            createEntryMatch(
+              'process.executable.caseless',
+
+              'C:\\Program Files\\Malware'
+            ),
+          ],
         }),
         {
           id: '123',
@@ -324,7 +389,9 @@ describe('mapping', () => {
           updated_at: '11/11/2011T11:11:11.111',
           updated_by: 'admin',
           os: OperatingSystem.WINDOWS,
-          entries: [createConditionEntry(ConditionEntryField.PATH, 'C:\\Program Files\\Malware')],
+          entries: [
+            createConditionEntry(ConditionEntryField.PATH, 'match', 'C:\\Program Files\\Malware'),
+          ],
         }
       );
     });
@@ -356,7 +423,7 @@ describe('mapping', () => {
           updated_at: '11/11/2011T11:11:11.111',
           updated_by: 'admin',
           os: OperatingSystem.WINDOWS,
-          entries: [createConditionEntry(ConditionEntryField.SIGNER, 'Microsoft Windows')],
+          entries: [createConditionEntry(ConditionEntryField.SIGNER, 'match', 'Microsoft Windows')],
         }
       );
     });
@@ -370,7 +437,13 @@ describe('mapping', () => {
           created_at: '11/11/2011T11:11:11.111',
           created_by: 'admin',
           os_types: ['linux'],
-          entries: [createEntryMatch('process.hash.md5', '1234234659af249ddf3e40864e9fb241')],
+          entries: [
+            createEntryMatch(
+              'process.hash.md5',
+
+              '1234234659af249ddf3e40864e9fb241'
+            ),
+          ],
         }),
         {
           id: '123',
@@ -384,7 +457,11 @@ describe('mapping', () => {
           updated_by: 'admin',
           os: OperatingSystem.LINUX,
           entries: [
-            createConditionEntry(ConditionEntryField.HASH, '1234234659af249ddf3e40864e9fb241'),
+            createConditionEntry(
+              ConditionEntryField.HASH,
+              'match',
+              '1234234659af249ddf3e40864e9fb241'
+            ),
           ],
         }
       );
@@ -400,7 +477,11 @@ describe('mapping', () => {
           created_by: 'admin',
           os_types: ['linux'],
           entries: [
-            createEntryMatch('process.hash.sha1', 'f635da961234234659af249ddf3e40864e9fb241'),
+            createEntryMatch(
+              'process.hash.sha1',
+
+              'f635da961234234659af249ddf3e40864e9fb241'
+            ),
           ],
         }),
         {
@@ -417,6 +498,7 @@ describe('mapping', () => {
           entries: [
             createConditionEntry(
               ConditionEntryField.HASH,
+              'match',
               'f635da961234234659af249ddf3e40864e9fb241'
             ),
           ],
@@ -436,6 +518,7 @@ describe('mapping', () => {
           entries: [
             createEntryMatch(
               'process.hash.sha256',
+
               'f635da96124659af249ddf3e40864e9fb234234659af249ddf3e40864e9fb241'
             ),
           ],
@@ -454,6 +537,7 @@ describe('mapping', () => {
           entries: [
             createConditionEntry(
               ConditionEntryField.HASH,
+              'match',
               'f635da96124659af249ddf3e40864e9fb234234659af249ddf3e40864e9fb241'
             ),
           ],
@@ -469,7 +553,7 @@ describe('mapping', () => {
         description: 'Linux Trusted App',
         effectScope: { type: 'global' },
         os: OperatingSystem.LINUX,
-        entries: [createConditionEntry(ConditionEntryField.PATH, '/bin/malware')],
+        entries: [createConditionEntry(ConditionEntryField.PATH, 'match', '/bin/malware')],
         version: 'abc',
       };
 
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 c6048e5725c88..786a74e91b51a 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
@@ -11,6 +11,7 @@ import { OsType } from '../../../../../lists/common/schemas';
 import {
   EntriesArray,
   EntryMatch,
+  EntryMatchWildcard,
   EntryNested,
   ExceptionListItemSchema,
   NestedEntriesArray,
@@ -28,6 +29,7 @@ import {
   OperatingSystem,
   TrustedApp,
   UpdateTrustedApp,
+  TrustedAppEntryTypes,
 } from '../../../../common/endpoint/types';
 
 type ConditionEntriesMap = { [K in ConditionEntryField]?: ConditionEntry<K> };
@@ -46,6 +48,7 @@ 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);
@@ -53,9 +56,10 @@ const filterUndefined = <T>(list: Array<T | undefined>): T[] => {
 
 export const createConditionEntry = <T extends ConditionEntryField>(
   field: T,
+  type: TrustedAppEntryTypes,
   value: string
 ): ConditionEntry<T> => {
-  return { field, value, type: 'match', operator: 'included' };
+  return { field, value, type, operator: OPERATOR_VALUE };
 };
 
 export const tagsToEffectScope = (tags: string[]): EffectScope => {
@@ -78,12 +82,23 @@ export const entriesToConditionEntriesMap = (entries: EntriesArray): ConditionEn
     if (entry.field.startsWith('process.hash') && entry.type === 'match') {
       return {
         ...result,
-        [ConditionEntryField.HASH]: createConditionEntry(ConditionEntryField.HASH, entry.value),
+        [ConditionEntryField.HASH]: createConditionEntry(
+          ConditionEntryField.HASH,
+          entry.type,
+          entry.value
+        ),
       };
-    } else if (entry.field === 'process.executable.caseless' && entry.type === 'match') {
+    } else if (
+      entry.field === 'process.executable.caseless' &&
+      (entry.type === 'match' || entry.type === 'wildcard')
+    ) {
       return {
         ...result,
-        [ConditionEntryField.PATH]: createConditionEntry(ConditionEntryField.PATH, entry.value),
+        [ConditionEntryField.PATH]: createConditionEntry(
+          ConditionEntryField.PATH,
+          entry.type,
+          entry.value
+        ),
       };
     } else if (entry.field === 'process.Ext.code_signature' && entry.type === 'nested') {
       const subjectNameCondition = entry.entries.find((subEntry): subEntry is EntryMatch => {
@@ -95,6 +110,7 @@ export const entriesToConditionEntriesMap = (entries: EntriesArray): ConditionEn
           ...result,
           [ConditionEntryField.SIGNER]: createConditionEntry(
             ConditionEntryField.SIGNER,
+            subjectNameCondition.type,
             subjectNameCondition.value
           ),
         };
@@ -166,7 +182,11 @@ const hashType = (hash: string): 'md5' | 'sha256' | 'sha1' | undefined => {
 };
 
 export const createEntryMatch = (field: string, value: string): EntryMatch => {
-  return { field, value, type: 'match', operator: 'included' };
+  return { field, value, type: 'match', operator: OPERATOR_VALUE };
+};
+
+export const createEntryMatchWildcard = (field: string, value: string): EntryMatchWildcard => {
+  return { field, value, type: 'wildcard', operator: OPERATOR_VALUE };
 };
 
 export const createEntryNested = (field: string, entries: NestedEntriesArray): EntryNested => {
@@ -193,6 +213,11 @@ export const conditionEntriesToEntries = (conditionEntries: ConditionEntry[]): E
         createEntryMatch('trusted', 'true'),
         createEntryMatch('subject_name', conditionEntry.value),
       ]);
+    } else if (
+      conditionEntry.field === ConditionEntryField.PATH &&
+      conditionEntry.type === 'wildcard'
+    ) {
+      return createEntryMatchWildcard(`process.executable.caseless`, conditionEntry.value);
     } else {
       return createEntryMatch(`process.executable.caseless`, conditionEntry.value);
     }
diff --git a/x-pack/plugins/security_solution/server/endpoint/routes/trusted_apps/service.test.ts b/x-pack/plugins/security_solution/server/endpoint/routes/trusted_apps/service.test.ts
index 42f4c6d157389..d99a89ce11137 100644
--- a/x-pack/plugins/security_solution/server/endpoint/routes/trusted_apps/service.test.ts
+++ b/x-pack/plugins/security_solution/server/endpoint/routes/trusted_apps/service.test.ts
@@ -65,8 +65,8 @@ const TRUSTED_APP: TrustedApp = {
   os: OperatingSystem.LINUX,
   effectScope: { type: 'global' },
   entries: [
-    createConditionEntry(ConditionEntryField.HASH, '1234234659af249ddf3e40864e9fb241'),
-    createConditionEntry(ConditionEntryField.PATH, '/bin/malware'),
+    createConditionEntry(ConditionEntryField.HASH, 'match', '1234234659af249ddf3e40864e9fb241'),
+    createConditionEntry(ConditionEntryField.PATH, 'match', '/bin/malware'),
   ],
 };
 
@@ -109,8 +109,35 @@ describe('service', () => {
         effectScope: { type: 'global' },
         os: OperatingSystem.LINUX,
         entries: [
-          createConditionEntry(ConditionEntryField.PATH, '/bin/malware'),
-          createConditionEntry(ConditionEntryField.HASH, '1234234659af249ddf3e40864e9fb241'),
+          createConditionEntry(ConditionEntryField.PATH, 'match', '/bin/malware'),
+          createConditionEntry(
+            ConditionEntryField.HASH,
+            'match',
+            '1234234659af249ddf3e40864e9fb241'
+          ),
+        ],
+      });
+
+      expect(result).toEqual({ data: TRUSTED_APP });
+
+      expect(exceptionsListClient.createTrustedAppsList).toHaveBeenCalled();
+    });
+
+    it('should create trusted app with correct wildcard type', async () => {
+      exceptionsListClient.createExceptionListItem.mockResolvedValue(EXCEPTION_LIST_ITEM);
+
+      const result = await createTrustedApp(exceptionsListClient, {
+        name: 'linux trusted app 1',
+        description: 'Linux trusted app 1',
+        effectScope: { type: 'global' },
+        os: OperatingSystem.LINUX,
+        entries: [
+          createConditionEntry(ConditionEntryField.PATH, 'wildcard', '/bin/malware'),
+          createConditionEntry(
+            ConditionEntryField.HASH,
+            'wildcard',
+            '1234234659af249ddf3e40864e9fb241'
+          ),
         ],
       });
 
diff --git a/x-pack/plugins/security_solution/server/endpoint/schemas/artifacts/lists.ts b/x-pack/plugins/security_solution/server/endpoint/schemas/artifacts/lists.ts
index 4c11325652f80..1b1370472f633 100644
--- a/x-pack/plugins/security_solution/server/endpoint/schemas/artifacts/lists.ts
+++ b/x-pack/plugins/security_solution/server/endpoint/schemas/artifacts/lists.ts
@@ -30,6 +30,24 @@ export const translatedEntryMatchMatcher = t.keyof({
 });
 export type TranslatedEntryMatchMatcher = t.TypeOf<typeof translatedEntryMatchMatcher>;
 
+export const translatedEntryMatchWildcardMatcher = t.keyof({
+  wildcard_cased: null,
+  wildcard_caseless: null,
+});
+export type TranslatedEntryMatchWildcardMatcher = t.TypeOf<
+  typeof translatedEntryMatchWildcardMatcher
+>;
+
+export const translatedEntryMatchWildcard = t.exact(
+  t.type({
+    field: t.string,
+    operator,
+    type: translatedEntryMatchWildcardMatcher,
+    value: t.string,
+  })
+);
+export type TranslatedEntryMatchWildcard = t.TypeOf<typeof translatedEntryMatchWildcard>;
+
 export const translatedEntryMatch = t.exact(
   t.type({
     field: t.string,
@@ -61,6 +79,7 @@ export type TranslatedEntryNested = t.TypeOf<typeof translatedEntryNested>;
 export const translatedEntry = t.union([
   translatedEntryNested,
   translatedEntryMatch,
+  translatedEntryMatchWildcard,
   translatedEntryMatchAny,
 ]);
 export type TranslatedEntry = t.TypeOf<typeof translatedEntry>;
diff --git a/x-pack/plugins/translations/translations/ja-JP.json b/x-pack/plugins/translations/translations/ja-JP.json
index fe9bf6eac14d0..746af100cb733 100644
--- a/x-pack/plugins/translations/translations/ja-JP.json
+++ b/x-pack/plugins/translations/translations/ja-JP.json
@@ -20118,7 +20118,6 @@
     "xpack.securitySolution.topN.closeButtonLabel": "閉じる",
     "xpack.securitySolution.topN.rawEventsSelectLabel": "未加工イベント",
     "xpack.securitySolution.trustedapps.aboutInfo": "パフォーマンスを改善したり、ホストで実行されている他のアプリケーションとの競合を解消したりするには、信頼できるアプリケーションを追加します。信頼できるアプリケーションは、Endpoint Securityを実行しているホストに適用されます。",
-    "xpack.securitySolution.trustedapps.card.operator.includes": "is",
     "xpack.securitySolution.trustedapps.card.removeButtonLabel": "削除",
     "xpack.securitySolution.trustedapps.create.conditionFieldValueRequiredMsg": "[{row}] フィールドエントリには値が必要です",
     "xpack.securitySolution.trustedapps.create.conditionRequiredMsg": "1つ以上のフィールド定義が必要です",
diff --git a/x-pack/plugins/translations/translations/zh-CN.json b/x-pack/plugins/translations/translations/zh-CN.json
index 7eab0f835a556..163d9af5eeafb 100644
--- a/x-pack/plugins/translations/translations/zh-CN.json
+++ b/x-pack/plugins/translations/translations/zh-CN.json
@@ -20439,7 +20439,6 @@
     "xpack.securitySolution.topN.closeButtonLabel": "关闭",
     "xpack.securitySolution.topN.rawEventsSelectLabel": "原始事件",
     "xpack.securitySolution.trustedapps.aboutInfo": "添加受信任的应用程序，以提高性能或缓解与主机上运行的其他应用程序的冲突。受信任的应用程序将应用于运行 Endpoint Security 的主机。",
-    "xpack.securitySolution.trustedapps.card.operator.includes": "是",
     "xpack.securitySolution.trustedapps.card.removeButtonLabel": "移除",
     "xpack.securitySolution.trustedapps.create.conditionFieldValueRequiredMsg": "[{row}] 字段条目必须包含值",
     "xpack.securitySolution.trustedapps.create.conditionRequiredMsg": "至少需要一个字段定义",