diff --git a/vscode-extension/extension.js b/vscode-extension/extension.js
index f79bbb7..acc58c1 100644
--- a/vscode-extension/extension.js
+++ b/vscode-extension/extension.js
@@ -84,12 +84,13 @@ async function configureHost() {
   });
   const sshDir = path.join(os.homedir(), '.ssh');
   fs.mkdirSync(sshDir, { recursive: true });
-  const generatedPath = expandHomePath(
+  const mainConfig = path.join(sshDir, 'config');
+  const generatedPath = resolveGeneratedSshConfigPath(
+    mainConfig,
     config.get('generatedSshConfig') || path.join(sshDir, 'config.dosh'),
     os.homedir(),
     process.platform
   );
-  const mainConfig = path.join(sshDir, 'config');
   ensureInclude(mainConfig, sshIncludeTarget(mainConfig, generatedPath, process.platform));
   upsertBlock(generatedPath, alias, block);
   return { alias, generatedPath };
@@ -143,6 +144,18 @@ function sshIncludeTarget(mainConfigPath, generatedPath, platform = process.plat
   return sshConfigPathWord(includePath, platform);
 }
 
+function resolveGeneratedSshConfigPath(
+  mainConfigPath,
+  configuredPath,
+  home = os.homedir(),
+  platform = process.platform
+) {
+  const pathApi = platform === 'win32' ? path.win32 : path;
+  const mainDir = pathApi.resolve(pathApi.dirname(mainConfigPath));
+  const expanded = expandHomePath(configuredPath, home, platform);
+  return pathApi.resolve(mainDir, expanded);
+}
+
 function upsertBlock(configPath, alias, block) {
   const dir = path.dirname(configPath);
   if (dir && dir !== '.') {
@@ -185,7 +198,9 @@ async function showSshConfig() {
   const api = requireVscode();
   const config = api.workspace.getConfiguration('dosh');
   const sshDir = path.join(os.homedir(), '.ssh');
-  const generatedPath = expandHomePath(
+  const mainConfig = path.join(sshDir, 'config');
+  const generatedPath = resolveGeneratedSshConfigPath(
+    mainConfig,
     config.get('generatedSshConfig') || path.join(sshDir, 'config.dosh'),
     os.homedir(),
     process.platform
@@ -270,6 +285,7 @@ module.exports = {
   deactivate,
   expandHomePath,
   ensureInclude,
+  resolveGeneratedSshConfigPath,
   sshBlock,
   sshConfigPathWord,
   shellQuote,
diff --git a/vscode-extension/extension.test.js b/vscode-extension/extension.test.js
index 27ce282..746e2b3 100644
--- a/vscode-extension/extension.test.js
+++ b/vscode-extension/extension.test.js
@@ -7,6 +7,7 @@ const path = require('node:path');
 const {
   expandHomePath,
   ensureInclude,
+  resolveGeneratedSshConfigPath,
   shellQuote,
   sshBlock,
   sshConfigPathWord,
@@ -101,6 +102,27 @@ test('home-relative generated config paths expand for POSIX and Windows', () =>
   );
 });
 
+test('relative generated config paths resolve beside the main ssh config', () => {
+  assert.equal(
+    resolveGeneratedSshConfigPath(
+      '/Users/palav/.ssh/config',
+      'config.dosh',
+      '/Users/palav',
+      'darwin'
+    ),
+    '/Users/palav/.ssh/config.dosh'
+  );
+  assert.equal(
+    resolveGeneratedSshConfigPath(
+      'C:\\Users\\palav\\.ssh\\config',
+      'dosh\\config.dosh',
+      'C:\\Users\\palav',
+      'win32'
+    ),
+    'C:\\Users\\palav\\.ssh\\dosh\\config.dosh'
+  );
+});
+
 test('config writers create missing parent directories', () => {
   const root = fs.mkdtempSync(path.join(os.tmpdir(), 'dosh-vscode-'));
   const mainConfig = path.join(root, 'ssh', 'config');