diff --git a/javascript/ql/lib/semmle/javascript/internal/PathResolution.qll b/javascript/ql/lib/semmle/javascript/internal/PathResolution.qll
index 56ad357a92e..3b3aea019f3 100644
--- a/javascript/ql/lib/semmle/javascript/internal/PathResolution.qll
+++ b/javascript/ql/lib/semmle/javascript/internal/PathResolution.qll
@@ -73,6 +73,16 @@ private module AutomaticFileExtensions {
 }
 
 module PathResolution {
+  /**
+   * Provides an extension point for mapping build directories to corresonding source directories.
+   */
+  class AdditionalBuildPathMapping extends Unit {
+    /**
+     * Gets a source directory whose contents are compiled to `base/buildDir`.
+     */
+    Container getSourceFromBuildTarget(Container base, string buildDir) { none() }
+  }
+
   /**
    * Holds if `path` is a relative path, in the sense that it must be resolved relative to
    * its enclosing directory.
@@ -352,7 +362,12 @@ module PathResolution {
 
     predicate shouldResolve(Container base, string path) { shouldResolve(_, base, path) }
 
-    predicate getAnAdditionalChild = AutomaticFileExtensions::getAnAdditionalChild/2;
+    // predicate getAnAdditionalChild = AutomaticFileExtensions::getAnAdditionalChild/2;
+    Container getAnAdditionalChild(Container base, string name) {
+      result = AutomaticFileExtensions::getAnAdditionalChild(base, name)
+      or
+      result = ReverseBuildDir::getAnAdditionalChild(base, name)
+    }
   }
 
   private module ResolvePathExpr = ResolvePaths<ResolvePathExprConfig>;
@@ -382,13 +397,7 @@ module PathResolution {
     Container getAnAdditionalChild(Container base, string name) {
       result = AutomaticFileExtensions::getAnAdditionalChild(base, name)
       or
-      // When resolving an output-like folder that doesn't exist, try resolving from 'src'
-      exists(Folder folder | base = folder |
-        folder = any(PackageJson pkg).getJsonFile().getParentContainer() and
-        name = getABuildOutputFolderName() and
-        not exists(folder.getChildContainer(name)) and
-        result = folder.getChildContainer(getASrcFolderName())
-      )
+      result = ReverseBuildDir::getAnAdditionalChild(base, name)
     }
   }
 
@@ -401,6 +410,33 @@ module PathResolution {
     )
   }
 
+  /**
+   * Provides a `getAnAdditionalChild` predicate for mapping files inside a build directory
+   * back to their corresponding source files.
+   */
+  private module ReverseBuildDir {
+    Container getAnAdditionalChild(Container base, string name) {
+      // Redirect './bar' to 'foo' given a tsconfig like:
+      //   { include: ["foo"], compilerOptions: { outDir: "./bar" }}
+      exists(TSConfig tsconfig |
+        name =
+          tsconfig.getCompilerOptions().getPropStringValue("outDir").regexpReplaceAll("^\\./", "") and
+        base = tsconfig.getFolder() and
+        result = tsconfig.getAnIncludedBaseContainer()
+      )
+      or
+      // Heuristic version of the above based on commonly used source and build folder names
+      exists(Folder folder | base = folder |
+        folder = any(PackageJson pkg).getJsonFile().getParentContainer() and
+        name = getABuildOutputFolderName() and
+        not exists(folder.getChildContainer(name)) and
+        result = folder.getChildContainer(getASrcFolderName())
+      )
+      or
+      result = any(AdditionalBuildPathMapping b).getSourceFromBuildTarget(base, name)
+    }
+  }
+
   /**
    * Gets a folder name that is a common source folder name.
    */
@@ -465,7 +501,7 @@ module PathResolution {
     final private class FinalPathExpr = PathExpr;
 
     class PathExprToDebug extends FinalPathExpr {
-      PathExprToDebug() { this.getValue() = "~/core/handlers/RequestHandler" }
+      PathExprToDebug() { this.getValue() = "ai" }
     }
 
     query PathExprToDebug pathExprs() { any() }
diff --git a/javascript/ql/test/library-tests/PathResolution/TSConfigOutDir/src/foo.ts b/javascript/ql/test/library-tests/PathResolution/TSConfigOutDir/src/foo.ts
new file mode 100644
index 00000000000..ad1d380d6cc
--- /dev/null
+++ b/javascript/ql/test/library-tests/PathResolution/TSConfigOutDir/src/foo.ts
@@ -0,0 +1 @@
+export const x = 1;
diff --git a/javascript/ql/test/library-tests/PathResolution/TSConfigOutDir/tsconfig.json b/javascript/ql/test/library-tests/PathResolution/TSConfigOutDir/tsconfig.json
new file mode 100644
index 00000000000..09d14078cb6
--- /dev/null
+++ b/javascript/ql/test/library-tests/PathResolution/TSConfigOutDir/tsconfig.json
@@ -0,0 +1,7 @@
+{
+    "include": ["src"],
+    "compilerOptions": {
+        // Use unusual name to test independently of naming heuristics
+        "outDir": "./customOutDir"
+    }
+}
diff --git a/javascript/ql/test/library-tests/PathResolution/import-packages.ts b/javascript/ql/test/library-tests/PathResolution/import-packages.ts
index c1399db994e..0a4e0e40086 100644
--- a/javascript/ql/test/library-tests/PathResolution/import-packages.ts
+++ b/javascript/ql/test/library-tests/PathResolution/import-packages.ts
@@ -22,3 +22,5 @@ import '@example/package-guess2'; // $ importTarget=PackageGuess2/blah/stuff.ts
 
 import './PackageWithMainExt'; // $ importTarget=PackageWithMainExt/lib/main.ts
 import '@example/package-with-main-ext'; // $ importTarget=PackageWithMainExt/lib/main.ts
+
+import './TSConfigOutDir/customOutDir/foo.js'; // $ importTarget=TSConfigOutDir/src/foo.ts
diff --git a/javascript/ql/test/library-tests/PathResolution/test.expected b/javascript/ql/test/library-tests/PathResolution/test.expected
index 3f139ac7b3d..8581258c23f 100644
--- a/javascript/ql/test/library-tests/PathResolution/test.expected
+++ b/javascript/ql/test/library-tests/PathResolution/test.expected
@@ -74,3 +74,4 @@
 | import-packages.ts:21:1:21:33 | import  ... uess2'; | PackageGuess2/blah/stuff.ts |
 | import-packages.ts:23:1:23:30 | import  ... inExt'; | PackageWithMainExt/lib/main.ts |
 | import-packages.ts:24:1:24:40 | import  ... n-ext'; | PackageWithMainExt/lib/main.ts |
+| import-packages.ts:26:1:26:46 | import  ... oo.js'; | TSConfigOutDir/src/foo.ts |