diff --git a/doc/api/packages.md b/doc/api/packages.md
index fb393eb823b7bf..ef55618c4137ca 100644
--- a/doc/api/packages.md
+++ b/doc/api/packages.md
@@ -485,7 +485,7 @@ where `import '#dep'` does not get the resolution of the external package
 file `./dep-polyfill.js` relative to the package in other environments.
 
 Unlike the `"exports"` field, the `"imports"` field permits mapping to external
-packages.
+packages and locations.
 
 The resolution rules for the imports field are otherwise analogous to the
 exports field.
diff --git a/lib/internal/modules/esm/resolve.js b/lib/internal/modules/esm/resolve.js
index f9673a3ed54571..758b8f582007ad 100644
--- a/lib/internal/modules/esm/resolve.js
+++ b/lib/internal/modules/esm/resolve.js
@@ -105,6 +105,9 @@ function emitInvalidSegmentDeprecation(target, request, match, pjsonUrl, interna
   }
   const pjsonPath = fileURLToPath(pjsonUrl);
   const double = RegExpPrototypeExec(doubleSlashRegEx, isTarget ? target : request) !== null;
+  console.trace({
+    target, request
+  })
   process.emitWarning(
     `Use of deprecated ${double ? 'double slash' :
       'leading or trailing slash matching'} resolving "${target}" for module ` +
@@ -355,6 +358,7 @@ const patternRegEx = /\*/g;
  * @param {boolean} internal - Whether the target is internal to the package.
  * @param {boolean} isPathMap - Whether the target is a path map.
  * @param {string[]} conditions - The import conditions.
+ * @param {boolean} mustBeInternalTarget - If target must be in the package boundary.
  * @returns {URL} - The resolved URL object.
  * @throws {ERR_INVALID_PACKAGE_TARGET} - If the target is invalid.
  * @throws {ERR_INVALID_SUBPATH} - If the subpath is invalid.
@@ -369,14 +373,15 @@ function resolvePackageTargetString(
   internal,
   isPathMap,
   conditions,
+  mustBeInternalTarget = true,
 ) {
 
   if (subpath !== '' && !pattern && target[target.length - 1] !== '/') {
     throw invalidPackageTarget(match, target, packageJSONUrl, internal, base);
   }
 
-  if (!StringPrototypeStartsWith(target, './')) {
-    if (internal && !StringPrototypeStartsWith(target, '../') &&
+  if (!StringPrototypeStartsWith(target, './') && !StringPrototypeStartsWith(target, '../')) {
+    if (internal &&
         !StringPrototypeStartsWith(target, '/')) {
       // No need to convert target to string, since it's already presumed to be
       if (!URLCanParse(target)) {
@@ -390,8 +395,17 @@ function resolvePackageTargetString(
     throw invalidPackageTarget(match, target, packageJSONUrl, internal, base);
   }
 
-  if (RegExpPrototypeExec(invalidSegmentRegEx, StringPrototypeSlice(target, 2)) !== null) {
-    if (RegExpPrototypeExec(deprecatedInvalidSegmentRegEx, StringPrototypeSlice(target, 2)) === null) {
+  // skip ../ and ./ prefixes when looking for invalid segments
+  const skipPrefix = target.length > 1 && target[0] === '.' ?
+    target[1] === '/' ?
+      2 :
+      target.length > 2 && target[1] === '.' && target[2] === '/' ?
+        3 :
+        0
+    :
+    0
+  if (RegExpPrototypeExec(invalidSegmentRegEx, StringPrototypeSlice(target, skipPrefix)) !== null) {
+    if (RegExpPrototypeExec(deprecatedInvalidSegmentRegEx, StringPrototypeSlice(target, skipPrefix)) === null) {
       if (!isPathMap) {
         const request = pattern ?
           StringPrototypeReplace(match, '*', () => subpath) :
@@ -410,7 +424,7 @@ function resolvePackageTargetString(
   const resolvedPath = resolved.pathname;
   const packagePath = new URL('.', packageJSONUrl).pathname;
 
-  if (!StringPrototypeStartsWith(resolvedPath, packagePath)) {
+  if (mustBeInternalTarget && !StringPrototypeStartsWith(resolvedPath, packagePath)) {
     throw invalidPackageTarget(match, target, packageJSONUrl, internal, base);
   }
 
@@ -461,14 +475,16 @@ function isArrayIndex(key) {
  * @param {boolean} internal - Whether the package is internal.
  * @param {boolean} isPathMap - Whether the package is a path map.
  * @param {Set<string>} conditions - The conditions to match.
+ * @param {boolean} mustBeInternalTarget - If the target must be in the package boundary. Used to restrict
+ *                                         targets to be inside of the package.json directory for "exports".
  * @returns {URL | null | undefined} - The resolved target, or null if not found, or undefined if not resolvable.
  */
 function resolvePackageTarget(packageJSONUrl, target, subpath, packageSubpath,
-                              base, pattern, internal, isPathMap, conditions) {
+                              base, pattern, internal, isPathMap, conditions, mustBeInternalTarget) {
   if (typeof target === 'string') {
     return resolvePackageTargetString(
       target, subpath, packageSubpath, packageJSONUrl, base, pattern, internal,
-      isPathMap, conditions);
+      isPathMap, conditions, mustBeInternalTarget);
   } else if (ArrayIsArray(target)) {
     if (target.length === 0) {
       return null;
@@ -481,7 +497,7 @@ function resolvePackageTarget(packageJSONUrl, target, subpath, packageSubpath,
       try {
         resolveResult = resolvePackageTarget(
           packageJSONUrl, targetItem, subpath, packageSubpath, base, pattern,
-          internal, isPathMap, conditions);
+          internal, isPathMap, conditions, mustBeInternalTarget);
       } catch (e) {
         lastException = e;
         if (e.code === 'ERR_INVALID_PACKAGE_TARGET') {
@@ -518,7 +534,7 @@ function resolvePackageTarget(packageJSONUrl, target, subpath, packageSubpath,
         const conditionalTarget = target[key];
         const resolveResult = resolvePackageTarget(
           packageJSONUrl, conditionalTarget, subpath, packageSubpath, base,
-          pattern, internal, isPathMap, conditions);
+          pattern, internal, isPathMap, conditions, mustBeInternalTarget);
         if (resolveResult === undefined) { continue; }
         return resolveResult;
       }
@@ -583,6 +599,7 @@ function packageExportsResolve(
     const resolveResult = resolvePackageTarget(
       packageJSONUrl, target, '', packageSubpath, base, false, false, false,
       conditions,
+      true,
     );
 
     if (resolveResult == null) {
@@ -635,7 +652,7 @@ function packageExportsResolve(
       true,
       false,
       StringPrototypeEndsWith(packageSubpath, '/'),
-      conditions);
+      conditions, true);
 
     if (resolveResult == null) {
       throw exportsNotFound(packageSubpath, packageJSONUrl, base);
@@ -693,6 +710,7 @@ function packageImportsResolve(name, base, conditions) {
         const resolveResult = resolvePackageTarget(
           packageJSONUrl, imports[name], '', name, base, false, true, false,
           conditions,
+          false,
         );
         if (resolveResult != null) {
           return resolveResult;
@@ -725,7 +743,8 @@ function packageImportsResolve(name, base, conditions) {
           const resolveResult = resolvePackageTarget(packageJSONUrl, target,
                                                      bestMatchSubpath,
                                                      bestMatch, base, true,
-                                                     true, false, conditions);
+                                                     true, false, conditions,
+                                                     false);
           if (resolveResult != null) {
             return resolveResult;
           }
diff --git a/test/es-module/test-esm-imports.mjs b/test/es-module/test-esm-imports.mjs
index 4b7e97eb8d2c5c..35b44c9c493de7 100644
--- a/test/es-module/test-esm-imports.mjs
+++ b/test/es-module/test-esm-imports.mjs
@@ -26,6 +26,10 @@ const { requireImport, importImport } = importer;
     ['#subpath//asdf.asdf', { default: 'test' }],
     // Double slash
     ['#subpath/as//df.asdf', { default: 'test' }],
+    // Target steps below the package base
+    ['#belowbase', { default: 'belowbase' }],
+    // Target steps uses pattern below the package base
+    ['#belowbase/nested', { default: 'nested' }],
   ]);
 
   for (const [validSpecifier, expected] of internalImports) {
@@ -38,8 +42,6 @@ const { requireImport, importImport } = importer;
   }
 
   const invalidImportTargets = new Set([
-    // Target steps below the package base
-    ['#belowbase', '#belowbase'],
     // Target is a URL
     ['#url', '#url'],
   ]);
diff --git a/test/fixtures/es-modules/belowbase.js b/test/fixtures/es-modules/belowbase.js
new file mode 100644
index 00000000000000..ad892195a79891
--- /dev/null
+++ b/test/fixtures/es-modules/belowbase.js
@@ -0,0 +1 @@
+module.exports = 'belowbase'
diff --git a/test/fixtures/es-modules/belowbase/nested.js b/test/fixtures/es-modules/belowbase/nested.js
new file mode 100644
index 00000000000000..895868ff0d1e79
--- /dev/null
+++ b/test/fixtures/es-modules/belowbase/nested.js
@@ -0,0 +1 @@
+module.exports = 'nested'
diff --git a/test/fixtures/es-modules/pkgimports/package.json b/test/fixtures/es-modules/pkgimports/package.json
index dbbbcd1ab01ea1..fb056228b9f7bf 100644
--- a/test/fixtures/es-modules/pkgimports/package.json
+++ b/test/fixtures/es-modules/pkgimports/package.json
@@ -11,7 +11,8 @@
     "#external": "pkgexports/valid-cjs",
     "#external/subpath/*": "pkgexports/sub/*",
     "#external/invalidsubpath/": "pkgexports/sub",
-    "#belowbase": "../belowbase",
+    "#belowbase": "../belowbase.js",
+    "#belowbase/*": "../belowbase/*.js",
     "#url": "some:url",
     "#null": null,
     "#nullcondition": {