diff --git a/packages/apidom-core/src/elements/SourceMap.ts b/packages/apidom-core/src/elements/SourceMap.ts
index 22cb2420b..bc4087d29 100644
--- a/packages/apidom-core/src/elements/SourceMap.ts
+++ b/packages/apidom-core/src/elements/SourceMap.ts
@@ -1,12 +1,12 @@
 import { ArrayElement, Element, Attributes, Meta } from 'minim';
 
-interface Position {
+export interface Position {
   row: number;
   column: number;
   char: number;
 }
 
-interface PositionRange {
+export interface PositionRange {
   start: Position;
   end: Position;
 }
diff --git a/packages/apidom-core/src/index.ts b/packages/apidom-core/src/index.ts
index d5fec1faa..54ecd6424 100644
--- a/packages/apidom-core/src/index.ts
+++ b/packages/apidom-core/src/index.ts
@@ -15,6 +15,7 @@ export { default as MediaTypes } from './media-types';
 
 export { Element, MemberElement, KeyValuePair, ObjectSlice, ArraySlice, refract } from 'minim';
 export type { NamespacePluginOptions, Attributes, Meta } from 'minim';
+export type { PositionRange, Position } from './elements/SourceMap';
 export { default as namespace, Namespace, createNamespace } from './namespace';
 
 export {
diff --git a/packages/apidom-json-pointer/src/compile.ts b/packages/apidom-json-pointer/src/compile.ts
index c0550f5dc..7a07d1443 100644
--- a/packages/apidom-json-pointer/src/compile.ts
+++ b/packages/apidom-json-pointer/src/compile.ts
@@ -1,12 +1,22 @@
 import escape from './escape';
+import CompilationJsonPointerError from './errors/CompilationJsonPointerError';
 
 // compile :: String[] -> String
 const compile = (tokens: string[]): string => {
-  if (tokens.length === 0) {
-    return '';
-  }
+  try {
+    if (tokens.length === 0) {
+      return '';
+    }
 
-  return `/${tokens.map(escape).join('/')}`;
+    return `/${tokens.map(escape).join('/')}`;
+  } catch (error: unknown) {
+    throw new CompilationJsonPointerError(
+      'JSON Pointer compilation of tokens encountered an error.',
+      {
+        tokens,
+      },
+    );
+  }
 };
 
 export default compile;
diff --git a/packages/apidom-json-pointer/src/errors/CompilationJsonPointerError.ts b/packages/apidom-json-pointer/src/errors/CompilationJsonPointerError.ts
new file mode 100644
index 000000000..698d970ba
--- /dev/null
+++ b/packages/apidom-json-pointer/src/errors/CompilationJsonPointerError.ts
@@ -0,0 +1,21 @@
+import { ApiDOMErrorOptions } from '@swagger-api/apidom-error';
+
+import JsonPointerError from './JsonPointerError';
+
+export interface CompilationJsonPointerErrorOptions extends ApiDOMErrorOptions {
+  readonly tokens: string[];
+}
+
+class CompilationJsonPointerError extends JsonPointerError {
+  public readonly tokens!: string[];
+
+  constructor(message?: string, structuredOptions?: CompilationJsonPointerErrorOptions) {
+    super(message, structuredOptions);
+
+    if (typeof structuredOptions !== 'undefined') {
+      this.tokens = [...structuredOptions.tokens];
+    }
+  }
+}
+
+export default CompilationJsonPointerError;
diff --git a/packages/apidom-json-pointer/src/errors/EvaluationJsonPointerError.ts b/packages/apidom-json-pointer/src/errors/EvaluationJsonPointerError.ts
index 605a2b386..b5d60a8bd 100644
--- a/packages/apidom-json-pointer/src/errors/EvaluationJsonPointerError.ts
+++ b/packages/apidom-json-pointer/src/errors/EvaluationJsonPointerError.ts
@@ -1,3 +1,45 @@
-import { ApiDOMError } from '@swagger-api/apidom-error';
+import { ApiDOMErrorOptions } from '@swagger-api/apidom-error';
+import { Element, hasElementSourceMap, toValue } from '@swagger-api/apidom-core';
 
-export default class EvaluationJsonPointerError extends ApiDOMError {}
+import JsonPointerError from './JsonPointerError';
+
+export interface EvaluationJsonPointerErrorOptions<T extends Element> extends ApiDOMErrorOptions {
+  readonly pointer: string;
+  readonly tokens?: string[];
+  readonly failedToken?: string;
+  readonly failedTokenPosition?: number;
+  readonly element: T;
+}
+
+class EvaluationJsonPointerError<T extends Element> extends JsonPointerError {
+  public readonly pointer!: string;
+
+  public readonly tokens?: string[];
+
+  public readonly failedToken?: string;
+
+  public readonly failedTokenPosition?: number;
+
+  public readonly element!: string;
+
+  public readonly elementSourceMap?: [[number, number, number], [number, number, number]];
+
+  constructor(message?: string, structuredOptions?: EvaluationJsonPointerErrorOptions<T>) {
+    super(message, structuredOptions);
+
+    if (typeof structuredOptions !== 'undefined') {
+      this.pointer = structuredOptions.pointer;
+      if (Array.isArray(structuredOptions.tokens)) {
+        this.tokens = [...structuredOptions.tokens];
+      }
+      this.failedToken = structuredOptions.failedToken;
+      this.failedTokenPosition = structuredOptions.failedTokenPosition;
+      this.element = structuredOptions.element.element;
+      if (hasElementSourceMap(structuredOptions.element)) {
+        this.elementSourceMap = toValue(structuredOptions.element.getMetaProperty('sourceMap'));
+      }
+    }
+  }
+}
+
+export default EvaluationJsonPointerError;
diff --git a/packages/apidom-json-pointer/src/errors/InvalidJsonPointerError.ts b/packages/apidom-json-pointer/src/errors/InvalidJsonPointerError.ts
index 001683e37..6c175d9a1 100644
--- a/packages/apidom-json-pointer/src/errors/InvalidJsonPointerError.ts
+++ b/packages/apidom-json-pointer/src/errors/InvalidJsonPointerError.ts
@@ -1,7 +1,21 @@
-import { ApiDOMError } from '@swagger-api/apidom-error';
+import { ApiDOMErrorOptions } from '@swagger-api/apidom-error';
 
-export default class InvalidJsonPointerError extends ApiDOMError {
-  constructor(pointer: string) {
-    super(`Invalid JSON Pointer "${pointer}". Pointers must begin with "/"`);
+import JsonPointerError from './JsonPointerError';
+
+export interface InvalidJsonPointerErrorOptions extends ApiDOMErrorOptions {
+  readonly pointer: string;
+}
+
+class InvalidJsonPointerError extends JsonPointerError {
+  public readonly pointer!: string;
+
+  constructor(message?: string, structuredOptions?: InvalidJsonPointerErrorOptions) {
+    super(message, structuredOptions);
+
+    if (typeof structuredOptions !== 'undefined') {
+      this.pointer = structuredOptions.pointer;
+    }
   }
 }
+
+export default InvalidJsonPointerError;
diff --git a/packages/apidom-json-pointer/src/errors/JsonPointerError.ts b/packages/apidom-json-pointer/src/errors/JsonPointerError.ts
new file mode 100644
index 000000000..1f15aa0ee
--- /dev/null
+++ b/packages/apidom-json-pointer/src/errors/JsonPointerError.ts
@@ -0,0 +1,5 @@
+import { ApiDOMStructuredError } from '@swagger-api/apidom-error';
+
+class JsonPointerError extends ApiDOMStructuredError {}
+
+export default JsonPointerError;
diff --git a/packages/apidom-json-pointer/src/errors/index.ts b/packages/apidom-json-pointer/src/errors/index.ts
deleted file mode 100644
index 21fd46029..000000000
--- a/packages/apidom-json-pointer/src/errors/index.ts
+++ /dev/null
@@ -1,2 +0,0 @@
-export { default as EvaluationJsonPointerError } from './EvaluationJsonPointerError';
-export { default as InvalidJsonPointerError } from './InvalidJsonPointerError';
diff --git a/packages/apidom-json-pointer/src/evaluate.ts b/packages/apidom-json-pointer/src/evaluate.ts
index 61d6c6e4b..e6425f02a 100644
--- a/packages/apidom-json-pointer/src/evaluate.ts
+++ b/packages/apidom-json-pointer/src/evaluate.ts
@@ -2,17 +2,38 @@ import { isInteger } from 'ramda-adjunct';
 import { Element, isObjectElement, isArrayElement } from '@swagger-api/apidom-core';
 
 import parse from './parse';
-import { EvaluationJsonPointerError } from './errors';
+import EvaluationJsonPointerError from './errors/EvaluationJsonPointerError';
 
 // evaluates JSON Pointer against ApiDOM fragment
 const evaluate = <T extends Element>(pointer: string, element: T): Element => {
-  const tokens = parse(pointer);
+  let tokens: string[];
 
-  return tokens.reduce((acc, token) => {
+  try {
+    tokens = parse(pointer);
+  } catch (error: unknown) {
+    throw new EvaluationJsonPointerError(
+      `JSON Pointer evaluation failed while parsing the pointer "${pointer}".`,
+      {
+        pointer,
+        element,
+      },
+    );
+  }
+
+  return tokens.reduce((acc, token, tokenPosition) => {
     if (isObjectElement(acc)) {
       // @ts-ignore
       if (!acc.hasKey(token)) {
-        throw new EvaluationJsonPointerError(`Evaluation failed on token: "${token}"`);
+        throw new EvaluationJsonPointerError(
+          `JSON Pointer evaluation failed while evaluating token "${token}" against an ObjectElement`,
+          {
+            pointer,
+            tokens,
+            failedToken: token,
+            failedTokenPosition: tokenPosition,
+            element: acc,
+          },
+        );
       }
       // @ts-ignore
       return acc.get(token);
@@ -20,13 +41,25 @@ const evaluate = <T extends Element>(pointer: string, element: T): Element => {
 
     if (isArrayElement(acc)) {
       if (!(token in acc.content) || !isInteger(Number(token))) {
-        throw new EvaluationJsonPointerError(`Evaluation failed on token: "${token}"`);
+        throw new EvaluationJsonPointerError(
+          `JSON Pointer evaluation failed while evaluating token "${token}" against an ArrayElement`,
+          { pointer, tokens, failedToken: token, failedTokenPosition: tokenPosition, element: acc },
+        );
       }
       // @ts-ignore
       return acc.get(Number(token));
     }
 
-    throw new EvaluationJsonPointerError(`Evaluation failed on token: "${token}"`);
+    throw new EvaluationJsonPointerError(
+      `JSON Pointer evaluation failed while evaluating token "${token}" against an unexpected Element`,
+      {
+        pointer,
+        tokens,
+        failedToken: token,
+        failedTokenPosition: tokenPosition,
+        element: acc,
+      },
+    );
   }, element);
 };
 
diff --git a/packages/apidom-json-pointer/src/index.ts b/packages/apidom-json-pointer/src/index.ts
index 5384fd738..23dfa8265 100644
--- a/packages/apidom-json-pointer/src/index.ts
+++ b/packages/apidom-json-pointer/src/index.ts
@@ -1,4 +1,10 @@
-export { InvalidJsonPointerError, EvaluationJsonPointerError } from './errors';
+export { default as JsonPointerError } from './errors/JsonPointerError';
+export { default as InvalidJsonPointerError } from './errors/InvalidJsonPointerError';
+export type { InvalidJsonPointerErrorOptions } from './errors/InvalidJsonPointerError';
+export { default as CompilationJsonPointerError } from './errors/CompilationJsonPointerError';
+export type { CompilationJsonPointerErrorOptions } from './errors/CompilationJsonPointerError';
+export { default as EvaluationJsonPointerError } from './errors/EvaluationJsonPointerError';
+export type { EvaluationJsonPointerErrorOptions } from './errors/EvaluationJsonPointerError';
 export { default as escape } from './escape';
 export { default as unescape } from './unescape';
 export { default as parse, uriToPointer } from './parse';
diff --git a/packages/apidom-json-pointer/src/parse.ts b/packages/apidom-json-pointer/src/parse.ts
index 294ae47b9..3cdf4de59 100644
--- a/packages/apidom-json-pointer/src/parse.ts
+++ b/packages/apidom-json-pointer/src/parse.ts
@@ -2,7 +2,7 @@ import { map, pipe, split, startsWith, tail } from 'ramda';
 import { isEmptyString, trimCharsStart } from 'ramda-adjunct';
 
 import unescape from './unescape';
-import { InvalidJsonPointerError } from './errors';
+import InvalidJsonPointerError from './errors/InvalidJsonPointerError';
 
 // parse :: String -> String[]
 const parse = (pointer: string): string[] => {
@@ -11,12 +11,25 @@ const parse = (pointer: string): string[] => {
   }
 
   if (!startsWith('/', pointer)) {
-    throw new InvalidJsonPointerError(pointer);
+    throw new InvalidJsonPointerError(
+      `Invalid JSON Pointer "${pointer}". JSON Pointers must begin with "/"`,
+      {
+        pointer,
+      },
+    );
   }
 
-  const tokens = pipe(split('/'), map(unescape))(pointer);
-
-  return tail(tokens);
+  try {
+    const tokens = pipe(split('/'), map(unescape))(pointer);
+    return tail(tokens);
+  } catch (error: unknown) {
+    throw new InvalidJsonPointerError(
+      `JSON Pointer parsing of "${pointer}" encountered an error.`,
+      {
+        pointer,
+      },
+    );
+  }
 };
 
 /**