diff --git a/lib/internal/modules/esm/resolve.js b/lib/internal/modules/esm/resolve.js
index bfee280212fc4d..7a8cc2114cade3 100644
--- a/lib/internal/modules/esm/resolve.js
+++ b/lib/internal/modules/esm/resolve.js
@@ -101,16 +101,16 @@ function emitTrailingSlashPatternDeprecation(match, pjsonUrl, base) {
 
 const doubleSlashRegEx = /[/\\][/\\]/;
 
-function emitInvalidSegmentDeprecation(target, request, match, pjsonUrl, base) {
+function emitInvalidSegmentDeprecation(target, request, match, pjsonUrl, internal, base, isTarget) {
   if (!pendingDeprecation) { return; }
   const pjsonPath = fileURLToPath(pjsonUrl);
-  const double = RegExpPrototypeExec(doubleSlashRegEx, target) !== null;
+  const double = RegExpPrototypeExec(doubleSlashRegEx, isTarget ? target : request) !== null;
   process.emitWarning(
     `Use of deprecated ${double ? 'double slash' :
       'leading or trailing slash matching'} resolving "${target}" for module ` +
       `request "${request}" ${request !== match ? `matched to "${match}" ` : ''
-      }in the "exports" field module resolution of the package at ${pjsonPath}${
-        base ? ` imported from ${fileURLToPath(base)}` : ''}.`,
+      }in the "${internal ? 'imports' : 'exports'}" field module resolution of the package at ${
+        pjsonPath}${base ? ` imported from ${fileURLToPath(base)}` : ''}.`,
     'DeprecationWarning',
     'DEP0166'
   );
@@ -438,7 +438,7 @@ function resolvePackageTargetString(
         const resolvedTarget = pattern ?
           RegExpPrototypeSymbolReplace(patternRegEx, target, () => subpath) :
           target;
-        emitInvalidSegmentDeprecation(resolvedTarget, request, match, packageJSONUrl, base);
+        emitInvalidSegmentDeprecation(resolvedTarget, request, match, packageJSONUrl, internal, base, true);
       }
     } else {
       throwInvalidPackageTarget(match, target, packageJSONUrl, internal, base);
@@ -461,7 +461,7 @@ function resolvePackageTargetString(
         const resolvedTarget = pattern ?
           RegExpPrototypeSymbolReplace(patternRegEx, target, () => subpath) :
           target;
-        emitInvalidSegmentDeprecation(resolvedTarget, request, match, packageJSONUrl, base);
+        emitInvalidSegmentDeprecation(resolvedTarget, request, match, packageJSONUrl, internal, base, false);
       }
     } else {
       throwInvalidSubpath(request, match, packageJSONUrl, internal, base);
diff --git a/snapshot.blob b/snapshot.blob
new file mode 100644
index 00000000000000..d2f936ee0f61d7
Binary files /dev/null and b/snapshot.blob differ
diff --git a/test/es-module/test-esm-imports-deprecations.mjs b/test/es-module/test-esm-imports-deprecations.mjs
new file mode 100644
index 00000000000000..775152f29ecc68
--- /dev/null
+++ b/test/es-module/test-esm-imports-deprecations.mjs
@@ -0,0 +1,27 @@
+// Flags: --pending-deprecation
+import { mustCall } from '../common/index.mjs';
+import assert from 'assert';
+
+let curWarning = 0;
+const expectedWarnings = [
+  'Use of deprecated double slash',
+  'Use of deprecated double slash',
+  './sub//null',
+  './sub/////null',
+  './sub//internal/test',
+  './sub//internal//test',
+  '#subpath/////internal',
+  '#subpath//asdf.asdf',
+  '#subpath/as//df.asdf',
+  './sub//null',
+  './sub/////null',
+  './sub//internal/test',
+  './sub//internal//test',
+  '#subpath/////internal',
+];
+
+process.addListener('warning', mustCall((warning) => {
+  assert(warning.stack.includes(expectedWarnings[curWarning++]), warning.stack);
+}, expectedWarnings.length));
+
+await import('./test-esm-imports.mjs');
diff --git a/test/es-module/test-esm-imports.mjs b/test/es-module/test-esm-imports.mjs
index a42738646fbaa8..2720f47974128a 100644
--- a/test/es-module/test-esm-imports.mjs
+++ b/test/es-module/test-esm-imports.mjs
@@ -22,6 +22,10 @@ const { requireImport, importImport } = importer;
     ['#external/subpath/asdf.js', { default: 'asdf' }],
     // Trailing pattern imports
     ['#subpath/asdf.asdf', { default: 'test' }],
+    // Leading slash
+    ['#subpath//asdf.asdf', { default: 'test' }],
+    // Double slash
+    ['#subpath/as//df.asdf', { default: 'test' }],
   ]);
 
   for (const [validSpecifier, expected] of internalImports) {
diff --git a/test/fixtures/es-modules/pkgimports/package.json b/test/fixtures/es-modules/pkgimports/package.json
index 6971e8b6fbcdea..dbbbcd1ab01ea1 100644
--- a/test/fixtures/es-modules/pkgimports/package.json
+++ b/test/fixtures/es-modules/pkgimports/package.json
@@ -1,6 +1,5 @@
 {
   "imports": {
-    "#test": "./test.js",
     "#branch": {
       "import": "./importbranch.js",
       "require": "./requirebranch.js"
@@ -26,6 +25,7 @@
     },
     "#subpath/nullshadow/*": [null],
     "#": "./test.js",
+    "#*est": "./*est.js",
     "#/initialslash": "./test.js",
     "#notfound": "./notfound.js",
     "#encodedslash": "./..%2F/x.js",