diff --git a/packages/definitions-parser/src/lib/definition-parser.ts b/packages/definitions-parser/src/lib/definition-parser.ts
index 781b297c60..871ea3610b 100644
--- a/packages/definitions-parser/src/lib/definition-parser.ts
+++ b/packages/definitions-parser/src/lib/definition-parser.ts
@@ -264,7 +264,12 @@ function getTypingDataForSingleTypesVersion(
 ): TypingDataFromIndividualTypeScriptVersion {
   const tsconfig = fs.readJson("tsconfig.json") as TsConfig;
   checkFilesFromTsConfig(packageName, tsconfig, fs.debugPath());
-  const { types, tests } = allReferencedFiles(tsconfig.files!, fs, packageName, packageDirectory);
+  const { types, tests, hasNonRelativeImports } = allReferencedFiles(
+    tsconfig.files!,
+    fs,
+    packageName,
+    packageDirectory
+  );
   const usedFiles = new Set([...types.keys(), ...tests.keys(), "tsconfig.json", "tslint.json"]);
   const otherFiles =
     ls.indexOf(unusedFilesName) > -1
@@ -289,6 +294,16 @@ function getTypingDataForSingleTypesVersion(
     filter(getTestDependencies(packageName, types, tests.keys(), dependenciesSet, fs), m => !declaredModulesSet.has(m))
   );
 
+  const { paths } = tsconfig.compilerOptions;
+  if (directoryVersion && hasNonRelativeImports && !(paths && `${packageName}/*` in paths)) {
+    const mapping = JSON.stringify([`${packageName}/v${formatTypingVersion(directoryVersion)}/*`]);
+    throw new Error(
+      `${packageName}: Older version ${formatTypingVersion(
+        directoryVersion
+      )} must have a "paths" entry of "${packageName}/*": ${mapping}`
+    );
+  }
+
   const { dependencies, pathMappings } = calculateDependencies(
     packageName,
     tsconfig,
diff --git a/packages/definitions-parser/src/lib/module-info.ts b/packages/definitions-parser/src/lib/module-info.ts
index 6e9b5f1abf..d98a69e54a 100644
--- a/packages/definitions-parser/src/lib/module-info.ts
+++ b/packages/definitions-parser/src/lib/module-info.ts
@@ -147,12 +147,13 @@ export function allReferencedFiles(
   fs: FS,
   packageName: string,
   baseDirectory: string
-): { types: Map<string, ts.SourceFile>; tests: Map<string, ts.SourceFile> } {
+): { types: Map<string, ts.SourceFile>; tests: Map<string, ts.SourceFile>; hasNonRelativeImports: boolean } {
   const seenReferences = new Set<string>();
   const types = new Map<string, ts.SourceFile>();
   const tests = new Map<string, ts.SourceFile>();
+  let hasNonRelativeImports = false;
   entryFilenames.forEach(text => recur({ text, exact: true }));
-  return { types, tests };
+  return { types, tests, hasNonRelativeImports };
 
   function recur({ text, exact }: Reference): void {
     if (seenReferences.has(text)) {
@@ -170,13 +171,14 @@ export function allReferencedFiles(
         tests.set(resolvedFilename, src);
       }
 
-      const refs = findReferencedFiles(
+      const { refs, hasNonRelativeImports: result } = findReferencedFiles(
         src,
         packageName,
         path.dirname(resolvedFilename),
         normalizeSlashes(path.relative(baseDirectory, fs.debugPath()))
       );
       refs.forEach(recur);
+      hasNonRelativeImports = hasNonRelativeImports || result;
     }
   }
 }
@@ -215,6 +217,7 @@ interface Reference {
  */
 function findReferencedFiles(src: ts.SourceFile, packageName: string, subDirectory: string, baseDirectory: string) {
   const refs: Reference[] = [];
+  let hasNonRelativeImports = false;
 
   for (const ref of src.referencedFiles) {
     // Any <reference path="foo"> is assumed to be local
@@ -235,9 +238,10 @@ function findReferencedFiles(src: ts.SourceFile, packageName: string, subDirecto
     }
     if (ref.startsWith(packageName + "/")) {
       addReference({ text: convertToRelativeReference(ref), exact: false });
+      hasNonRelativeImports = true;
     }
   }
-  return refs;
+  return { refs, hasNonRelativeImports };
 
   function addReference(ref: Reference): void {
     // `path.normalize` may add windows slashes
diff --git a/packages/definitions-parser/test/definition-parser.test.ts b/packages/definitions-parser/test/definition-parser.test.ts
index b8bca117ee..26543accb5 100644
--- a/packages/definitions-parser/test/definition-parser.test.ts
+++ b/packages/definitions-parser/test/definition-parser.test.ts
@@ -73,27 +73,40 @@ describe(getTypingInfo, () => {
         const dt = createMockDT();
         dt.addOldVersionOfPackage("jquery", "3");
 
-        expect(getTypingInfo("jquery", dt.pkgFS("jquery"))).rejects.toMatchObject({
-          message:
-            "The latest version of the 'jquery' package is 3.3, so the subdirectory 'v3' is not allowed; " +
+        return expect(getTypingInfo("jquery", dt.pkgFS("jquery"))).rejects.toThrow(
+          "The latest version of the 'jquery' package is 3.3, so the subdirectory 'v3' is not allowed; " +
             "since it applies to any 3.* version, up to and including 3.3."
-        });
+        );
       });
 
       it("throws if a directory exists for the latest minor version", () => {
         const dt = createMockDT();
         dt.addOldVersionOfPackage("jquery", "3.3");
 
-        expect(getTypingInfo("jquery", dt.pkgFS("jquery"))).rejects.toMatchObject({
-          message: "The latest version of the 'jquery' package is 3.3, so the subdirectory 'v3.3' is not allowed."
-        });
+        return expect(getTypingInfo("jquery", dt.pkgFS("jquery"))).rejects.toThrow(
+          "The latest version of the 'jquery' package is 3.3, so the subdirectory 'v3.3' is not allowed."
+        );
       });
 
       it("does not throw when a minor version is older than the latest", () => {
         const dt = createMockDT();
         dt.addOldVersionOfPackage("jquery", "3.0");
 
-        expect(getTypingInfo("jquery", dt.pkgFS("jquery"))).resolves.toBeDefined();
+        return expect(getTypingInfo("jquery", dt.pkgFS("jquery"))).resolves.toBeDefined();
+      });
+
+      it("checks that older versions with non-relative imports have wildcard path mappings", () => {
+        const dt = createMockDT();
+        const jquery = dt.pkgDir("jquery");
+        jquery.set(
+          "JQuery.d.ts",
+          `import "jquery/component";
+`
+        );
+        dt.addOldVersionOfPackage("jquery", "1");
+        return expect(getTypingInfo("jquery", dt.pkgFS("jquery"))).rejects.toThrow(
+          'jquery: Older version 1 must have a "paths" entry of "jquery/*": ["jquery/v1/*"]'
+        );
       });
     });
   });