diff --git a/packages/cli/src/config/rollup.config.js b/packages/cli/src/config/rollup.config.js
index 8aa6f56c2..dc0d582d6 100644
--- a/packages/cli/src/config/rollup.config.js
+++ b/packages/cli/src/config/rollup.config.js
@@ -274,20 +274,33 @@ function greenwoodImportMetaUrl(compilation) {
 // TODO could we use this instead?
 // https://github.com/rollup/rollup/blob/v2.79.1/docs/05-plugin-development.md#resolveimportmeta
 // https://github.com/ProjectEvergreen/greenwood/issues/1087
-function greenwoodPatchSsrPagesEntryPointRuntimeImport() {
+function greenwoodPatchSsrPagesEntryPointRuntimeImport(compilation) {
   return {
     name: 'greenwood-patch-ssr-pages-entry-point-runtime-import',
     generateBundle(options, bundle) {
+      const { pagesDir, scratchDir } = compilation.context;
+
       Object.keys(bundle).forEach((key) => {
-        if (key.startsWith('__')) {
-          // ___GWD_ENTRY_FILE_URL=${filename}___
+        // map rollup bundle names back to original SSR pages for output bundles and paths
+        if (key.startsWith('_')) {
           const needle = bundle[key].code.match(/___GWD_ENTRY_FILE_URL=(.*.)___/);
-          if (needle) {
+
+          // handle windows shenanigans for facadeModuleId and path separators
+          if (new URL(`file://${bundle[key].facadeModuleId}`).pathname.startsWith(scratchDir.pathname) && needle) {
             const entryPathMatch = needle[1];
 
-            bundle[key].code = bundle[key].code.replace(/'___GWD_ENTRY_FILE_URL=(.*.)___'/, `new URL('./_${entryPathMatch}', import.meta.url)`);
-          } else {
-            console.warn(`Could not find entry path match for bundle => ${key}`);
+            Object.keys(bundle).forEach((_) => {
+              // handle windows shenanigans for facadeModuleId and path separators
+              if (new URL(`file://${bundle[_].facadeModuleId}`).pathname === `${pagesDir.pathname}${entryPathMatch}`) {
+                bundle[key].code = bundle[key].code.replace(/'___GWD_ENTRY_FILE_URL=(.*.)___'/, `new URL('./${bundle[_].fileName}', import.meta.url)`);
+
+                compilation.graph.forEach((page, idx) => {
+                  if (page.relativeWorkspacePagePath === `/${entryPathMatch}`) {
+                    compilation.graph[idx].outputPath = key;
+                  }
+                });
+              }
+            });
           }
         }
       });
@@ -405,7 +418,7 @@ const getRollupConfigForSsr = async (compilation, input) => {
       }),
       commonjs(),
       greenwoodImportMetaUrl(compilation),
-      greenwoodPatchSsrPagesEntryPointRuntimeImport() // TODO a little hacky but works for now
+      greenwoodPatchSsrPagesEntryPointRuntimeImport(compilation) // TODO a little hacky but works for now
     ],
     onwarn: (errorObj) => {
       const { code, message } = errorObj;
diff --git a/packages/cli/src/lifecycles/bundle.js b/packages/cli/src/lifecycles/bundle.js
index e5a28fdd5..4aad70159 100644
--- a/packages/cli/src/lifecycles/bundle.js
+++ b/packages/cli/src/lifecycles/bundle.js
@@ -190,9 +190,10 @@ async function bundleSsrPages(compilation) {
 
     for (const page of compilation.graph) {
       if (page.isSSR && !page.prerender) {
-        const { filename, imports, route, template, title } = page;
-        const entryFileUrl = new URL(`./_${filename}`, scratchDir);
-        const moduleUrl = new URL(`./${filename}`, pagesDir);
+        const { imports, route, template, title, relativeWorkspacePagePath } = page;
+        const entryFileUrl = new URL(`./_${relativeWorkspacePagePath.replace('/', '')}`, scratchDir);
+        const moduleUrl = new URL(`./${relativeWorkspacePagePath.replace('/', '')}`, pagesDir);
+        const outputPathRootUrl = new URL(`file://${path.dirname(entryFileUrl.pathname)}`);
         const request = new Request(moduleUrl); // TODO not really sure how to best no-op this?
         // TODO getTemplate has to be static (for now?)
         // https://github.com/ProjectEvergreen/greenwood/issues/955
@@ -205,6 +206,12 @@ async function bundleSsrPages(compilation) {
         staticHtml = await (await htmlOptimizer.optimize(new URL(`http://localhost:8080${route}`), new Response(staticHtml))).text();
         staticHtml = staticHtml.replace(/[`\\$]/g, '\\$&'); // https://stackoverflow.com/a/75688937/417806
 
+        if (!await checkResourceExists(outputPathRootUrl)) {
+          await fs.mkdir(outputPathRootUrl, {
+            recursive: true
+          });
+        }
+
         // better way to write out this inline code?
         await fs.writeFile(entryFileUrl, `
           import { executeRouteModule } from '${normalizePathnameForWindows(executeModuleUrl)}';
@@ -212,7 +219,7 @@ async function bundleSsrPages(compilation) {
           export async function handler(request) {
             const compilation = JSON.parse('${JSON.stringify(compilation)}');
             const page = JSON.parse('${JSON.stringify(page)}');
-            const moduleUrl = '___GWD_ENTRY_FILE_URL=${filename}___';
+            const moduleUrl = '___GWD_ENTRY_FILE_URL=${relativeWorkspacePagePath.replace('/', '')}___';
             const data = await executeRouteModule({ moduleUrl, compilation, page, request });
             let staticHtml = \`${staticHtml}\`;
 
diff --git a/packages/cli/src/lifecycles/graph.js b/packages/cli/src/lifecycles/graph.js
index ae82285e6..40b95f7a9 100644
--- a/packages/cli/src/lifecycles/graph.js
+++ b/packages/cli/src/lifecycles/graph.js
@@ -191,6 +191,7 @@ const generateGraph = async (compilation) => {
              * data: custom page frontmatter
              * filename: base filename of the page
              * id: filename without the extension
+             * relativeWorkspacePagePath: the file path relative to the user's workspace directory
              * label: "pretty" text representation of the filename
              * imports: per page JS or CSS file imports to be included in HTML output from frontmatter
              * resources: sum of all resources for the entire page
@@ -206,6 +207,7 @@ const generateGraph = async (compilation) => {
               data: customData || {},
               filename,
               id,
+              relativeWorkspacePagePath: relativePagePath,
               label: id.split('-')
                 .map((idPart) => {
                   return `${idPart.charAt(0).toUpperCase()}${idPart.substring(1)}`;
diff --git a/packages/cli/src/lifecycles/serve.js b/packages/cli/src/lifecycles/serve.js
index 678750374..7c94c29a8 100644
--- a/packages/cli/src/lifecycles/serve.js
+++ b/packages/cli/src/lifecycles/serve.js
@@ -294,7 +294,7 @@ async function getHybridServer(compilation) {
       const request = transformKoaRequestIntoStandardRequest(url, ctx.request);
 
       if (!config.prerender && matchingRoute.isSSR && !matchingRoute.prerender) {
-        const { handler } = await import(new URL(`./__${matchingRoute.filename}`, outputDir));
+        const { handler } = await import(new URL(`./${matchingRoute.outputPath}`, outputDir));
         const response = await handler(request, compilation);
 
         ctx.body = Readable.from(response.body);
diff --git a/packages/cli/src/plugins/resource/plugin-standard-html.js b/packages/cli/src/plugins/resource/plugin-standard-html.js
index 8f0622545..b64fcee64 100644
--- a/packages/cli/src/plugins/resource/plugin-standard-html.js
+++ b/packages/cli/src/plugins/resource/plugin-standard-html.js
@@ -105,7 +105,7 @@ class StandardHtmlResource extends ResourceInterface {
     }
 
     if (matchingRoute.isSSR) {
-      const routeModuleLocationUrl = new URL(`./${matchingRoute.filename}`, pagesDir);
+      const routeModuleLocationUrl = new URL(`.${matchingRoute.relativeWorkspacePagePath}`, pagesDir);
       const routeWorkerUrl = this.compilation.config.plugins.find(plugin => plugin.type === 'renderer').provider().executeModuleUrl;
 
       await new Promise(async (resolve, reject) => {
diff --git a/packages/cli/test/cases/build.plugins.context/theme-pack-context-plugin.js b/packages/cli/test/cases/build.plugins.context/theme-pack-context-plugin.js
index bff573f54..2227fbad2 100644
--- a/packages/cli/test/cases/build.plugins.context/theme-pack-context-plugin.js
+++ b/packages/cli/test/cases/build.plugins.context/theme-pack-context-plugin.js
@@ -1,20 +1,15 @@
 import fs from 'fs/promises';
-import os from 'os';
-import { spawnSync } from 'child_process';
 
 const packageJson = JSON.parse(await fs.readFile(new URL('./package.json', import.meta.url), 'utf-8'));
-const myThemePackPlugin = () => [{
+const myThemePackPlugin = (options = {}) => [{
   type: 'context',
   name: 'my-theme-pack:context',
   provider: () => {
     const { name } = packageJson;
-    const command = os.platform() === 'win32' ? 'npm.cmd' : 'npm';
-    const ls = spawnSync(command, ['ls', name]);
 
-    const isInstalled = ls.stdout.toString().indexOf('(empty)') < 0;
-    const templateLocation = isInstalled
-      ? new URL(`./node_modules/${name}/dist/layouts/`, import.meta.url)
-      : new URL('./fixtures/layouts/', import.meta.url);
+    const templateLocation = options.__isDevelopment // eslint-disable-line no-underscore-dangle
+      ? new URL('./fixtures/layouts/', import.meta.url)
+      : new URL(`./node_modules/${name}/dist/layouts/`, import.meta.url);
 
     return {
       templates: [
diff --git a/packages/cli/test/cases/develop.plugins.context/greenwood.config.js b/packages/cli/test/cases/develop.plugins.context/greenwood.config.js
index 74c311257..60eaf3c94 100644
--- a/packages/cli/test/cases/develop.plugins.context/greenwood.config.js
+++ b/packages/cli/test/cases/develop.plugins.context/greenwood.config.js
@@ -24,7 +24,9 @@ class MyThemePackDevelopmentResource extends ResourceInterface {
 
 export default {
   plugins: [
-    ...myThemePackPlugin(),
+    ...myThemePackPlugin({
+      __isDevelopment: true
+    }),
     {
       type: 'resource',
       name: 'my-theme-pack:resource',
diff --git a/packages/cli/test/cases/develop.ssr/develop.ssr.spec.js b/packages/cli/test/cases/develop.ssr/develop.ssr.spec.js
index 4f7919f66..18ecbccbf 100644
--- a/packages/cli/test/cases/develop.ssr/develop.ssr.spec.js
+++ b/packages/cli/test/cases/develop.ssr/develop.ssr.spec.js
@@ -16,6 +16,9 @@
  *   components/
  *     footer.js
  *   pages/
+ *     blog
+ *       first-post.js
+ *       index.js
  *     artists.js
  *     post.js
  *   templates/
@@ -284,6 +287,94 @@ describe('Develop Greenwood With: ', function() {
         expect(paragraph[0].textContent).to.not.be.undefined;
       });
     });
+
+    describe('Develop command with HTML route response using default export and nested SSR Blog Index page', function() {
+      let response = {};
+      let dom = {};
+      let body;
+
+      before(async function() {
+        response = await fetch(`${hostname}/blog/`);
+        body = await response.clone().text();
+        dom = new JSDOM(body);
+      });
+
+      it('should return a 200 status', function(done) {
+        expect(response.status).to.equal(200);
+        done();
+      });
+
+      it('should return the correct content type', function(done) {
+        expect(response.headers.get('content-type')).to.equal('text/html');
+        done();
+      });
+
+      it('should return a response body', function(done) {
+        expect(body).to.not.be.undefined;
+        done();
+      });
+
+      it('should be valid HTML from JSDOM', function(done) {
+        expect(dom).to.not.be.undefined;
+        done();
+      });
+
+      it('should be valid HTML from JSDOM', function(done) {
+        expect(dom).to.not.be.undefined;
+        done();
+      });
+
+      it('should have the expected postId as an <h1> tag in the body', function() {
+        const heading = dom.window.document.querySelectorAll('body > h1');
+
+        expect(heading.length).to.equal(1);
+        expect(heading[0].textContent).to.equal('Nested SSR page should work!');
+      });
+    });
+
+    describe('Develop command with HTML route response using default export and nested SSR Blog First Post page', function() {
+      let response = {};
+      let dom = {};
+      let body;
+
+      before(async function() {
+        response = await fetch(`${hostname}/blog/first-post/`);
+        body = await response.clone().text();
+        dom = new JSDOM(body);
+      });
+
+      it('should return a 200 status', function(done) {
+        expect(response.status).to.equal(200);
+        done();
+      });
+
+      it('should return the correct content type', function(done) {
+        expect(response.headers.get('content-type')).to.equal('text/html');
+        done();
+      });
+
+      it('should return a response body', function(done) {
+        expect(body).to.not.be.undefined;
+        done();
+      });
+
+      it('should be valid HTML from JSDOM', function(done) {
+        expect(dom).to.not.be.undefined;
+        done();
+      });
+
+      it('should be valid HTML from JSDOM', function(done) {
+        expect(dom).to.not.be.undefined;
+        done();
+      });
+
+      it('should have the expected postId as an <h1> tag in the body', function() {
+        const heading = dom.window.document.querySelectorAll('body > h1');
+
+        expect(heading.length).to.equal(1);
+        expect(heading[0].textContent).to.equal('Nested SSR First Post page should work!');
+      });
+    });
   });
 
   after(function() {
diff --git a/packages/cli/test/cases/develop.ssr/src/pages/blog/first-post.js b/packages/cli/test/cases/develop.ssr/src/pages/blog/first-post.js
new file mode 100644
index 000000000..d65087023
--- /dev/null
+++ b/packages/cli/test/cases/develop.ssr/src/pages/blog/first-post.js
@@ -0,0 +1,7 @@
+export default class BlogFirstPostPage extends HTMLElement {
+  connectedCallback() {
+    this.innerHTML = `
+      <h1>Nested SSR First Post page should work!</h1>
+    `;
+  }
+}
\ No newline at end of file
diff --git a/packages/cli/test/cases/develop.ssr/src/pages/blog/index.js b/packages/cli/test/cases/develop.ssr/src/pages/blog/index.js
new file mode 100644
index 000000000..331617673
--- /dev/null
+++ b/packages/cli/test/cases/develop.ssr/src/pages/blog/index.js
@@ -0,0 +1,7 @@
+export default class BlogPage extends HTMLElement {
+  connectedCallback() {
+    this.innerHTML = `
+      <h1>Nested SSR page should work!</h1>
+    `;
+  }
+}
\ No newline at end of file
diff --git a/packages/cli/test/cases/serve.default.ssr/serve.default.ssr.spec.js b/packages/cli/test/cases/serve.default.ssr/serve.default.ssr.spec.js
index 7a4b01b35..393ca909a 100644
--- a/packages/cli/test/cases/serve.default.ssr/serve.default.ssr.spec.js
+++ b/packages/cli/test/cases/serve.default.ssr/serve.default.ssr.spec.js
@@ -23,6 +23,9 @@
  *   pages/
  *     about.md
  *     artists.js
+ *     blog/
+ *       first-post.js
+ *       index.js
  *     index.js
  *     post.js
  *     users.js
@@ -272,6 +275,94 @@ describe('Serve Greenwood With: ', function() {
       });
     });
 
+    describe('Serve command with HTML route response using default export and nested SSR Blog Index page', function() {
+      let response = {};
+      let dom = {};
+      let body;
+
+      before(async function() {
+        response = await fetch(`${hostname}/blog/`);
+        body = await response.clone().text();
+        dom = new JSDOM(body);
+      });
+
+      it('should return a 200 status', function(done) {
+        expect(response.status).to.equal(200);
+        done();
+      });
+
+      it('should return the correct content type', function(done) {
+        expect(response.headers.get('content-type')).to.equal('text/html');
+        done();
+      });
+
+      it('should return a response body', function(done) {
+        expect(body).to.not.be.undefined;
+        done();
+      });
+
+      it('should be valid HTML from JSDOM', function(done) {
+        expect(dom).to.not.be.undefined;
+        done();
+      });
+
+      it('should be valid HTML from JSDOM', function(done) {
+        expect(dom).to.not.be.undefined;
+        done();
+      });
+
+      it('should have the expected postId as an <h1> tag in the body', function() {
+        const heading = dom.window.document.querySelectorAll('body > h1');
+
+        expect(heading.length).to.equal(1);
+        expect(heading[0].textContent).to.equal('Nested SSR page should work!');
+      });
+    });
+
+    describe('Develop command with HTML route response using default export and nested SSR Blog First Post page', function() {
+      let response = {};
+      let dom = {};
+      let body;
+
+      before(async function() {
+        response = await fetch(`${hostname}/blog/first-post/`);
+        body = await response.clone().text();
+        dom = new JSDOM(body);
+      });
+
+      it('should return a 200 status', function(done) {
+        expect(response.status).to.equal(200);
+        done();
+      });
+
+      it('should return the correct content type', function(done) {
+        expect(response.headers.get('content-type')).to.equal('text/html');
+        done();
+      });
+
+      it('should return a response body', function(done) {
+        expect(body).to.not.be.undefined;
+        done();
+      });
+
+      it('should be valid HTML from JSDOM', function(done) {
+        expect(dom).to.not.be.undefined;
+        done();
+      });
+
+      it('should be valid HTML from JSDOM', function(done) {
+        expect(dom).to.not.be.undefined;
+        done();
+      });
+
+      it('should have the expected postId as an <h1> tag in the body', function() {
+        const heading = dom.window.document.querySelectorAll('body > h1');
+
+        expect(heading.length).to.equal(1);
+        expect(heading[0].textContent).to.equal('Nested SSR First Post page should work!');
+      });
+    });
+
     describe('Bundled image using new URL and import.meta.url', function() {
       const bundledName = 'assets/logo-abb2e884.svg';
       let response = {};
diff --git a/packages/cli/test/cases/serve.default.ssr/src/pages/blog/first-post.js b/packages/cli/test/cases/serve.default.ssr/src/pages/blog/first-post.js
new file mode 100644
index 000000000..d65087023
--- /dev/null
+++ b/packages/cli/test/cases/serve.default.ssr/src/pages/blog/first-post.js
@@ -0,0 +1,7 @@
+export default class BlogFirstPostPage extends HTMLElement {
+  connectedCallback() {
+    this.innerHTML = `
+      <h1>Nested SSR First Post page should work!</h1>
+    `;
+  }
+}
\ No newline at end of file
diff --git a/packages/cli/test/cases/serve.default.ssr/src/pages/blog/index.js b/packages/cli/test/cases/serve.default.ssr/src/pages/blog/index.js
new file mode 100644
index 000000000..331617673
--- /dev/null
+++ b/packages/cli/test/cases/serve.default.ssr/src/pages/blog/index.js
@@ -0,0 +1,7 @@
+export default class BlogPage extends HTMLElement {
+  connectedCallback() {
+    this.innerHTML = `
+      <h1>Nested SSR page should work!</h1>
+    `;
+  }
+}
\ No newline at end of file
diff --git a/www/pages/docs/data.md b/www/pages/docs/data.md
index 530afc393..c7e60cfe4 100644
--- a/www/pages/docs/data.md
+++ b/www/pages/docs/data.md
@@ -62,6 +62,8 @@ graph {
 
   outputPath, // (string) the relative path to write to when generating static HTML
 
+  relativeWorkspacePagePath, // the file path relative to the user's workspace directory
+
   path, // (string) path to the file
 
   route,  // (string) A URL, typically derived from the filesystem path, e.g. /blog/2019/first-post/