diff --git a/vscode-extension/extension.js b/vscode-extension/extension.js
index f65b5fd..668698e 100644
--- a/vscode-extension/extension.js
+++ b/vscode-extension/extension.js
@@ -86,7 +86,7 @@ async function configureHost() {
   fs.mkdirSync(sshDir, { recursive: true });
   const generatedPath = config.get('generatedSshConfig') || path.join(sshDir, 'config.dosh');
   const mainConfig = path.join(sshDir, 'config');
-  ensureInclude(mainConfig, path.basename(generatedPath));
+  ensureInclude(mainConfig, sshIncludeTarget(mainConfig, generatedPath, process.platform));
   upsertBlock(generatedPath, alias, block);
   return { alias, generatedPath };
 }
@@ -123,6 +123,18 @@ function ensureInclude(configPath, includeFile) {
   fs.writeFileSync(configPath, `Include ${includeFile}\n${raw ? `\n${raw}` : ''}`);
 }
 
+function sshIncludeTarget(mainConfigPath, generatedPath, platform = process.platform) {
+  const pathApi = platform === 'win32' ? path.win32 : path;
+  const mainDir = pathApi.resolve(pathApi.dirname(mainConfigPath));
+  const generatedAbsolute = pathApi.resolve(mainDir, generatedPath);
+  const generatedDir = pathApi.resolve(pathApi.dirname(generatedAbsolute));
+  const includePath =
+    normalizeCase(generatedDir, platform) === normalizeCase(mainDir, platform)
+      ? pathApi.basename(generatedAbsolute)
+      : generatedAbsolute;
+  return sshConfigPathWord(includePath, platform);
+}
+
 function upsertBlock(configPath, alias, block) {
   const raw = fs.existsSync(configPath) ? fs.readFileSync(configPath, 'utf8') : '';
   const begin = `# BEGIN DOSH ${alias}`;
@@ -189,6 +201,18 @@ function sshConfigWord(value, platform = process.platform) {
   return shellQuote(value);
 }
 
+function sshConfigPathWord(value, platform = process.platform) {
+  const normalized = platform === 'win32' ? value.replace(/\\/g, '/') : value;
+  if (/^[a-zA-Z0-9_./:@%+=,-]+$/.test(normalized)) {
+    return normalized;
+  }
+  return `"${normalized.replace(/["\\]/g, '\\$&')}"`;
+}
+
+function normalizeCase(value, platform) {
+  return platform === 'win32' ? value.toLowerCase() : value;
+}
+
 function windowsCommandWord(value) {
   let out = '"';
   let backslashes = 0;
@@ -218,7 +242,9 @@ module.exports = {
   activate,
   deactivate,
   sshBlock,
+  sshConfigPathWord,
   shellQuote,
+  sshIncludeTarget,
   sshConfigWord,
   windowsCommandWord
 };
diff --git a/vscode-extension/extension.test.js b/vscode-extension/extension.test.js
index 1dba3ec..4e4fc81 100644
--- a/vscode-extension/extension.test.js
+++ b/vscode-extension/extension.test.js
@@ -4,6 +4,8 @@ const assert = require('node:assert/strict');
 const {
   shellQuote,
   sshBlock,
+  sshConfigPathWord,
+  sshIncludeTarget,
   sshConfigWord,
   windowsCommandWord
 } = require('./extension');
@@ -48,3 +50,36 @@ test('ssh block quotes proxy command for the target platform', () => {
   );
   assert.doesNotMatch(block, /'C:\\Program Files\\Dosh\\dosh\.exe'/);
 });
+
+test('ssh include target stays relative for generated config beside main config', () => {
+  assert.equal(
+    sshIncludeTarget('/Users/palav/.ssh/config', '/Users/palav/.ssh/config.dosh', 'darwin'),
+    'config.dosh'
+  );
+});
+
+test('ssh include target uses absolute path for custom generated config location', () => {
+  assert.equal(
+    sshIncludeTarget(
+      '/Users/palav/.ssh/config',
+      '/Users/palav/Library/Application Support/Dosh/config.dosh',
+      'darwin'
+    ),
+    '"/Users/palav/Library/Application Support/Dosh/config.dosh"'
+  );
+});
+
+test('ssh include target handles Windows custom generated config paths', () => {
+  assert.equal(
+    sshIncludeTarget(
+      'C:\\Users\\palav\\.ssh\\config',
+      'C:\\Users\\palav\\AppData\\Roaming\\Dosh Remote\\config.dosh',
+      'win32'
+    ),
+    '"C:/Users/palav/AppData/Roaming/Dosh Remote/config.dosh"'
+  );
+  assert.equal(
+    sshConfigPathWord('C:\\Users\\palav\\.ssh\\config.dosh', 'win32'),
+    'C:/Users/palav/.ssh/config.dosh'
+  );
+});