diff --git a/packages/cspell-lib/src/lib/Settings/Controller/configLoader/configLoader.test.ts b/packages/cspell-lib/src/lib/Settings/Controller/configLoader/configLoader.test.ts
index 334621efa48..adee1efe3dc 100644
--- a/packages/cspell-lib/src/lib/Settings/Controller/configLoader/configLoader.test.ts
+++ b/packages/cspell-lib/src/lib/Settings/Controller/configLoader/configLoader.test.ts
@@ -16,12 +16,17 @@ import {
     pathRepoTestFixturesURL,
 } from '../../../../test-util/test.locations.cjs';
 import { logError, logWarning } from '../../../util/logger.js';
-import { resolveFileWithURL, toFilePathOrHref, toFileUrl } from '../../../util/url.js';
+import { cwdURL, resolveFileWithURL, toFilePathOrHref, toFileUrl } from '../../../util/url.js';
 import { currentSettingsFileVersion, defaultConfigFileModuleRef, ENV_CSPELL_GLOB_ROOT } from '../../constants.js';
 import type { ImportFileRefWithError } from '../../CSpellSettingsServer.js';
 import { extractDependencies, getSources, mergeSettings } from '../../CSpellSettingsServer.js';
 import { _defaultSettings, getDefaultBundledSettingsAsync } from '../../DefaultSettings.js';
-import { __testing__ as __configLoader_testing__, createConfigLoader, loadPnP } from './configLoader.js';
+import {
+    __testing__ as __configLoader_testing__,
+    ConfigurationLoaderFailedToResolveError,
+    createConfigLoader,
+    loadPnP,
+} from './configLoader.js';
 import { configToRawSettings } from './configToRawSettings.js';
 import {
     clearCachedSettingsFiles,
@@ -38,7 +43,7 @@ import { extractImportErrors, extractImports } from './extractImportErrors.js';
 import { readSettings } from './readSettings.js';
 import { readSettingsFiles } from './readSettingsFiles.js';
 
-const { validateRawConfigVersion, resolveGlobRoot } = __configLoader_testing__;
+const { validateRawConfigVersion, resolveGlobRoot, relativeToCwd } = __configLoader_testing__;
 
 const rootCspellLib = path.join(pathPackageRoot, '.');
 const root = pathRepoRoot;
@@ -337,10 +342,10 @@ describe('Validate search/load config files', () => {
         clearCachedSettingsFiles();
     });
 
-    function resolveError(filename: string): ImportFileRefWithError {
+    function resolveError(filename: string, relativeTo = cwdURL()): ImportFileRefWithError {
         return {
             filename,
-            error: new Error(`Failed to resolve file: "${filename}"`),
+            error: new ConfigurationLoaderFailedToResolveError(filename, relativeTo),
         };
     }
 
@@ -803,6 +808,22 @@ describe('Validate Dependencies', () => {
     });
 });
 
+describe('relativeToCwd', () => {
+    test.each`
+        filename                                      | expected
+        ${cwdURL()}                                   | ${'./'}
+        ${'../../cspell.json'}                        | ${'../../cspell.json'}
+        ${'../../cspell.json'}                        | ${'../../cspell.json'}
+        ${'../../../cspell.json'}                     | ${'../../../cspell.json'}
+        ${pathToFileURL('../../../../cspell.json')}   | ${path.resolve('../../../../cspell.json')}
+        ${pathToFileURL('./samples/cspell.json')}     | ${'./samples/cspell.json'}
+        ${pathToFileURL('../samples/cspell.json')}    | ${'../samples/cspell.json'}
+        ${new URL('https://example.com/cspell.json')} | ${'https://example.com/cspell.json'}
+    `('relativeToCwd', ({ filename, expected }) => {
+        expect(relativeToCwd(filename)).toEqual(expected);
+    });
+});
+
 /**
  * Resolve relative to src/lib
  */
diff --git a/packages/cspell-lib/src/lib/Settings/Controller/configLoader/configLoader.ts b/packages/cspell-lib/src/lib/Settings/Controller/configLoader/configLoader.ts
index 258186efd37..b2759bfef60 100644
--- a/packages/cspell-lib/src/lib/Settings/Controller/configLoader/configLoader.ts
+++ b/packages/cspell-lib/src/lib/Settings/Controller/configLoader/configLoader.ts
@@ -21,6 +21,7 @@ import {
     cwdURL,
     resolveFileWithURL,
     toFilePathOrHref,
+    toFileUrl,
     windowsDriveLetterToUpper,
 } from '../../../util/url.js';
 import {
@@ -550,7 +551,7 @@ export class ConfigLoader implements IConfigLoader {
 
         return {
             filename: r.filename.startsWith('file:/') ? fileURLToPath(r.filename) : r.filename,
-            error: r.found ? undefined : new Error(`Failed to resolve file: "${filename}"`),
+            error: r.found ? undefined : new ConfigurationLoaderFailedToResolveError(filename, relativeTo),
         };
     }
 
@@ -677,9 +678,59 @@ async function isDirectory(fs: VFileSystem, path: URL): Promise<boolean> {
     }
 }
 
+export class ConfigurationLoaderError extends Error {
+    constructor(
+        message: string,
+        public readonly configurationFile?: string,
+        public readonly relativeTo?: string | URL,
+        cause?: unknown,
+    ) {
+        super(message);
+        this.name = 'Configuration Loader Error';
+        if (cause) {
+            this.cause = cause;
+        }
+    }
+}
+
+export class ConfigurationLoaderFailedToResolveError extends ConfigurationLoaderError {
+    constructor(
+        public readonly configurationFile: string,
+        public readonly relativeTo: string | URL,
+        cause?: unknown,
+    ) {
+        const filename = configurationFile.startsWith('file:/') ? fileURLToPath(configurationFile) : configurationFile;
+        const relSource = relativeToCwd(relativeTo);
+
+        const message = `Failed to resolve configuration file: "${filename}" referenced from "${relSource}"`;
+        super(message, configurationFile, relativeTo, cause);
+        // this.name = 'Configuration Loader Error';
+    }
+}
+
+function relativeToCwd(file: string | URL): string {
+    const url = toFileUrl(file);
+    const cwdPath = cwdURL().pathname.split('/').slice(0, -1);
+    const urlPath = url.pathname.split('/');
+    if (urlPath[0] !== cwdPath[0]) return toFilePathOrHref(file);
+    let i = 0;
+    for (; i < cwdPath.length; ++i) {
+        if (cwdPath[i] !== urlPath[i]) break;
+    }
+    const segments = cwdPath.length - i;
+    if (segments > 3) return toFilePathOrHref(file);
+    const prefix = '.'
+        .repeat(segments)
+        .split('')
+        .map(() => '..')
+        .join('/');
+    return [prefix || '.', ...urlPath.slice(i)].join('/');
+}
+
 export const __testing__ = {
     getDefaultConfigLoaderInternal,
     normalizeCacheSettings,
     validateRawConfigVersion,
     resolveGlobRoot,
+    relativeToCwd,
 };
diff --git a/packages/cspell-lib/src/lib/spellCheckFile.test.ts b/packages/cspell-lib/src/lib/spellCheckFile.test.ts
index d09ca585e57..e67742de169 100644
--- a/packages/cspell-lib/src/lib/spellCheckFile.test.ts
+++ b/packages/cspell-lib/src/lib/spellCheckFile.test.ts
@@ -276,7 +276,9 @@ function errNoEnt(file: string): Error {
 
 function eFailed(file: string): Error {
     return oc({
-        message: expectToEqualCaseInsensitive(`Failed to resolve file: "${rpS(file)}"`),
+        message: expectToEqualCaseInsensitive(
+            `Failed to resolve configuration file: "${rpS(file)}" referenced from "./"`,
+        ),
     });
 }
 
diff --git a/packages/cspell/src/app/__snapshots__/app.test.ts.snap b/packages/cspell/src/app/__snapshots__/app.test.ts.snap
index f486fe65be3..14f6c8a4be7 100644
--- a/packages/cspell/src/app/__snapshots__/app.test.ts.snap
+++ b/packages/cspell/src/app/__snapshots__/app.test.ts.snap
@@ -328,7 +328,7 @@ exports[`Validate cli > app 'cspell-bad.json' Expect Error: undefined 3`] = `
 exports[`Validate cli > app 'cspell-import-missing.json' Expect Error: [Function CheckFailed] 1`] = `[]`;
 
 exports[`Validate cli > app 'cspell-import-missing.json' Expect Error: [Function CheckFailed] 2`] = `
-"error	Configuration Error: Failed to resolve file: "../intentionally-missing-file.json"
+"error	Configuration Configuration Loader Error: Failed to resolve configuration file: "../intentionally-missing-file.json" referenced from "./samples/linked/cspell-import-missing.json"
 error	CSpell: Files checked: 0, Issues found: 0 in 0 files"
 `;