diff --git a/package-lock.json b/package-lock.json
index f21c6c7a4..66281f547 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -34635,6 +34635,7 @@
       "dependencies": {
         "@babel/runtime-corejs3": "^7.20.7",
         "@swagger-api/apidom-core": "^0.75.0",
+        "@swagger-api/apidom-error": "^0.75.0",
         "@swagger-api/apidom-json-pointer": "^0.75.0",
         "jsonpath-plus": "^7.2.0"
       }
diff --git a/packages/apidom-json-path/package.json b/packages/apidom-json-path/package.json
index 9fac646fb..367ec996e 100644
--- a/packages/apidom-json-path/package.json
+++ b/packages/apidom-json-path/package.json
@@ -39,6 +39,7 @@
   "dependencies": {
     "@babel/runtime-corejs3": "^7.20.7",
     "@swagger-api/apidom-core": "^0.75.0",
+    "@swagger-api/apidom-error": "^0.75.0",
     "@swagger-api/apidom-json-pointer": "^0.75.0",
     "jsonpath-plus": "^7.2.0"
   },
diff --git a/packages/apidom-json-path/src/errors/EvaluationJsonPathError.ts b/packages/apidom-json-path/src/errors/EvaluationJsonPathError.ts
new file mode 100644
index 000000000..e398611c5
--- /dev/null
+++ b/packages/apidom-json-path/src/errors/EvaluationJsonPathError.ts
@@ -0,0 +1,31 @@
+import { Element, hasElementSourceMap, toValue } from '@swagger-api/apidom-core';
+import { ApiDOMErrorOptions } from '@swagger-api/apidom-error';
+
+import JsonPathError from './JsonPathError';
+
+export interface EvaluationJsonPathErrorOptions<T extends Element> extends ApiDOMErrorOptions {
+  path: string | string[];
+  element: T;
+}
+
+class EvaluationJsonPathError<T extends Element> extends JsonPathError {
+  public readonly path!: string | string[];
+
+  public readonly element!: string;
+
+  public readonly elementSourceMap?: [[number, number, number], [number, number, number]];
+
+  constructor(message?: string, structuredOptions?: EvaluationJsonPathErrorOptions<T>) {
+    super(message, structuredOptions);
+
+    if (typeof structuredOptions !== 'undefined') {
+      this.path = structuredOptions.path;
+      this.element = structuredOptions.element.element;
+      if (hasElementSourceMap(structuredOptions.element)) {
+        this.elementSourceMap = toValue(structuredOptions.element.getMetaProperty('sourceMap'));
+      }
+    }
+  }
+}
+
+export default EvaluationJsonPathError;
diff --git a/packages/apidom-json-path/src/errors/JsonPathError.ts b/packages/apidom-json-path/src/errors/JsonPathError.ts
new file mode 100644
index 000000000..e2e03a6ba
--- /dev/null
+++ b/packages/apidom-json-path/src/errors/JsonPathError.ts
@@ -0,0 +1,5 @@
+import { ApiDOMStructuredError } from '@swagger-api/apidom-error';
+
+class JsonPathError extends ApiDOMStructuredError {}
+
+export default JsonPathError;
diff --git a/packages/apidom-json-path/src/errors/MultiEvaluationJsonPathError.ts b/packages/apidom-json-path/src/errors/MultiEvaluationJsonPathError.ts
new file mode 100644
index 000000000..849f2c5f4
--- /dev/null
+++ b/packages/apidom-json-path/src/errors/MultiEvaluationJsonPathError.ts
@@ -0,0 +1,31 @@
+import { Element, hasElementSourceMap, toValue } from '@swagger-api/apidom-core';
+import { ApiDOMErrorOptions } from '@swagger-api/apidom-error';
+
+import JsonPathError from './JsonPathError';
+
+export interface MultiEvaluationJsonPathErrorOptions<T extends Element> extends ApiDOMErrorOptions {
+  paths: string[] | string[][];
+  element: T;
+}
+
+class MultiEvaluationJsonPathError<T extends Element> extends JsonPathError {
+  public readonly paths!: string[] | string[][];
+
+  public readonly element!: string;
+
+  public readonly elementSourceMap?: [[number, number, number], [number, number, number]];
+
+  constructor(message?: string, structuredOptions?: MultiEvaluationJsonPathErrorOptions<T>) {
+    super(message, structuredOptions);
+
+    if (typeof structuredOptions !== 'undefined') {
+      this.paths = structuredOptions.paths;
+      this.element = structuredOptions.element.element;
+      if (hasElementSourceMap(structuredOptions.element)) {
+        this.elementSourceMap = toValue(structuredOptions.element.getMetaProperty('sourceMap'));
+      }
+    }
+  }
+}
+
+export default MultiEvaluationJsonPathError;
diff --git a/packages/apidom-json-path/src/evaluate-multi.ts b/packages/apidom-json-path/src/evaluate-multi.ts
index abe6e5188..b8e2733f4 100644
--- a/packages/apidom-json-path/src/evaluate-multi.ts
+++ b/packages/apidom-json-path/src/evaluate-multi.ts
@@ -2,6 +2,8 @@ import { JSONPath } from 'jsonpath-plus';
 import { Element, toValue } from '@swagger-api/apidom-core';
 import { evaluate as jsonPointerEvaluate } from '@swagger-api/apidom-json-pointer';
 
+import MultiEvaluationJsonPathError from './errors/MultiEvaluationJsonPathError';
+
 type JSONPathEvalTuple = [string, Element[]];
 
 type EvaluateMulti = {
@@ -13,30 +15,41 @@ type EvaluateMulti = {
  * Evaluates multiple JSONPaths on ApiDOM element.
  */
 const evaluateMulti: EvaluateMulti = (paths, element) => {
-  const json = toValue(element);
-  const results: JSONPathEvalTuple[] = [];
-
-  for (const path of paths) {
-    const pointers = JSONPath({
-      path,
-      json,
-      resultType: 'pointer',
-    }) as string[];
-
-    const endPointValues: Element[] = [];
-    for (const pointer of pointers) {
-      const endPointValue = jsonPointerEvaluate(pointer, element);
-      endPointValues.push(endPointValue);
+  try {
+    const json = toValue(element);
+    const results: JSONPathEvalTuple[] = [];
+
+    for (const path of paths) {
+      const pointers = JSONPath({
+        path,
+        json,
+        resultType: 'pointer',
+      }) as string[];
+
+      const endPointValues: Element[] = [];
+      for (const pointer of pointers) {
+        const endPointValue = jsonPointerEvaluate(pointer, element);
+        endPointValues.push(endPointValue);
+      }
+
+      if (Array.isArray(path)) {
+        results.push([JSONPath.toPathString(path), endPointValues]);
+      } else {
+        results.push([path, endPointValues]);
+      }
     }
 
-    if (Array.isArray(path)) {
-      results.push([JSONPath.toPathString(path), endPointValues]);
-    } else {
-      results.push([path, endPointValues]);
-    }
+    return results;
+  } catch (error: unknown) {
+    throw new MultiEvaluationJsonPathError(
+      `JSON Path evaluation failed while multi-evaluating "${String(paths)}".`,
+      {
+        paths,
+        element,
+        cause: error,
+      },
+    );
   }
-
-  return results;
 };
 
 export default evaluateMulti;
diff --git a/packages/apidom-json-path/src/evaluate.ts b/packages/apidom-json-path/src/evaluate.ts
index 6adb43faa..bfd327644 100644
--- a/packages/apidom-json-path/src/evaluate.ts
+++ b/packages/apidom-json-path/src/evaluate.ts
@@ -2,6 +2,8 @@ import { JSONPath } from 'jsonpath-plus';
 import { Element, toValue } from '@swagger-api/apidom-core';
 import { evaluate as jsonPointerEvaluate } from '@swagger-api/apidom-json-pointer';
 
+import EvaluationJsonPathError from './errors/EvaluationJsonPathError';
+
 type Evaluate = {
   <T extends Element>(path: string, element: T): Element[];
   <T extends Element>(path: string[], element: T): Element[];
@@ -11,14 +13,21 @@ type Evaluate = {
  * Evaluates single JSONPath on ApiDOM element.
  */
 const evaluate: Evaluate = (path, element) => {
-  const json = toValue(element);
-  const pointers = JSONPath({
-    path,
-    json,
-    resultType: 'pointer',
-  }) as string[];
+  try {
+    const json = toValue(element);
+    const pointers = JSONPath({
+      path,
+      json,
+      resultType: 'pointer',
+    }) as string[];
 
-  return pointers.map((pointer) => jsonPointerEvaluate(pointer, element));
+    return pointers.map((pointer) => jsonPointerEvaluate(pointer, element));
+  } catch (error: unknown) {
+    throw new EvaluationJsonPathError(
+      `JSON Path evaluation failed while evaluating "${String(path)}".`,
+      { path, element, cause: error },
+    );
+  }
 };
 
 export default evaluate;
diff --git a/packages/apidom-json-path/src/index.ts b/packages/apidom-json-path/src/index.ts
index ec2a73298..12649c845 100644
--- a/packages/apidom-json-path/src/index.ts
+++ b/packages/apidom-json-path/src/index.ts
@@ -1,2 +1,6 @@
+export { default as EvaluationJsonPathError } from './errors/EvaluationJsonPathError';
+export type { EvaluationJsonPathErrorOptions } from './errors/EvaluationJsonPathError';
+export { default as MultiEvaluationJsonPathError } from './errors/MultiEvaluationJsonPathError';
+export type { MultiEvaluationJsonPathErrorOptions } from './errors/MultiEvaluationJsonPathError';
 export { default as evaluate } from './evaluate';
 export { default as evaluateMulti } from './evaluate-multi';
diff --git a/packages/apidom-json-pointer/src/compile.ts b/packages/apidom-json-pointer/src/compile.ts
index 7a07d1443..393dfec49 100644
--- a/packages/apidom-json-pointer/src/compile.ts
+++ b/packages/apidom-json-pointer/src/compile.ts
@@ -14,6 +14,7 @@ const compile = (tokens: string[]): string => {
       'JSON Pointer compilation of tokens encountered an error.',
       {
         tokens,
+        cause: error,
       },
     );
   }
diff --git a/packages/apidom-json-pointer/src/evaluate.ts b/packages/apidom-json-pointer/src/evaluate.ts
index e6425f02a..964a48a8d 100644
--- a/packages/apidom-json-pointer/src/evaluate.ts
+++ b/packages/apidom-json-pointer/src/evaluate.ts
@@ -16,6 +16,7 @@ const evaluate = <T extends Element>(pointer: string, element: T): Element => {
       {
         pointer,
         element,
+        cause: error,
       },
     );
   }
diff --git a/packages/apidom-json-pointer/src/parse.ts b/packages/apidom-json-pointer/src/parse.ts
index 3cdf4de59..0df7d699f 100644
--- a/packages/apidom-json-pointer/src/parse.ts
+++ b/packages/apidom-json-pointer/src/parse.ts
@@ -27,6 +27,7 @@ const parse = (pointer: string): string[] => {
       `JSON Pointer parsing of "${pointer}" encountered an error.`,
       {
         pointer,
+        cause: error,
       },
     );
   }