diff --git a/lib/mapper.js b/lib/mapper.js
index 0c4b19a..9ab1ff3 100644
--- a/lib/mapper.js
+++ b/lib/mapper.js
@@ -23,6 +23,7 @@ var updateFromJson = function (path, map) {
         host: keyToSession[key]["host"],
         port: parseInt(keyToSession[key]["port"]),
         requires_path_in_url: info?.requires_path_in_url,
+        requires_path_in_header: info?.requires_path_in_header,
       },
     };
   }
@@ -66,6 +67,7 @@ var updateFromSqlite = function (path, map) {
           key_type: row["key_type"],
           token: row["token"],
           requires_path_in_url: info?.requires_path_in_url,
+          requires_path_in_header: info?.requires_path_in_header,
         };
       },
       finish,
diff --git a/lib/proxy.js b/lib/proxy.js
index 1532168..2565bc6 100644
--- a/lib/proxy.js
+++ b/lib/proxy.js
@@ -124,6 +124,15 @@ DynamicProxy.prototype.targetForRequest = function (request) {
     key = path_split[1];
     token = path_split[2];
 
+    const target_inject_header = this.sessionMap[key]?.requires_path_in_header;
+    if (target_inject_header) {
+      request.headers[target_inject_header] = [
+        this.proxyPathPrefix,
+        key,
+        token,
+      ].join("/");
+    }
+
     if (!this.sessionMap[key]?.requires_path_in_url) {
       const target_url = "/" + path_split.slice(3).join("/");
       request.url = target_url;
diff --git a/test/test.js b/test/test.js
index 2e5c464..8bc17a1 100644
--- a/test/test.js
+++ b/test/test.js
@@ -245,6 +245,46 @@ describe("DynamicProxy", function () {
     });
   });
 
+  describe("map based path forwarding to top-level path with entry point path in header", function () {
+    it(
+      'should respect session map with requires_path_in_header="X-My-Header", strip entry point path from ' +
+        'url and instead provide it in header "X-My-Header"',
+      async function () {
+        const sessionMap = {
+          coolkey: {
+            token: "cooltoken",
+            target: {
+              host: "localhost",
+              port: TEST_PORT,
+            },
+            requires_path_in_header: "X-My-Header",
+          },
+        };
+        const proxy = new DynamicProxy({
+          port: 5103,
+          verbose: true,
+          sessionMap: sessionMap,
+          proxyPathPrefix: "/interactivetool/ep",
+        });
+        proxy.listen();
+        const headers = {
+          host: "usegalaxy.org",
+        };
+
+        proxy.proxy.on("proxyReq", function (proxyReq) {
+          proxyReq
+            .getHeader("X-My-Header")
+            .should.equal("/interactivetool/ep/coolkey/cooltoken");
+        });
+
+        const path =
+          "/interactivetool/ep/coolkey/cooltoken/test_data/extradir/README.md";
+        await verifyProxyOnPort(5103, headers, path);
+        proxy.close();
+      },
+    );
+  });
+
   describe("double proxying", function () {
     it("should proxy across two servers", async function () {
       const sessionMap = {