diff --git a/packages/insomnia-inso/src/__tests__/write-file.test.js b/packages/insomnia-inso/src/__tests__/write-file.test.js
index b1b1280d89..9996da3a16 100644
--- a/packages/insomnia-inso/src/__tests__/write-file.test.js
+++ b/packages/insomnia-inso/src/__tests__/write-file.test.js
@@ -4,6 +4,7 @@ import { writeFileWithCliOptions } from '../write-file';
 import mkdirp from 'mkdirp';
 import fs from 'fs';
 import { InsoError } from '../errors';
+import os from 'os';
 
 jest.mock('mkdirp', () => ({
   sync: jest.fn().mockResolvedValue(),
@@ -32,6 +33,26 @@ describe('writeFileWithCliOptions', () => {
     await expect(promise).resolves.toBe('file.yaml');
   });
 
+  it('should write to absolute output file', async () => {
+    const absolutePath = path.join(os.tmpdir(), 'dev', 'file.yaml');
+    const output = absolutePath;
+    const contents = 'contents';
+    const workingDir = undefined;
+
+    const promise = writeFileWithCliOptions(output, contents, workingDir);
+    await expect(promise).resolves.toBe(absolutePath);
+  });
+
+  it('should write to absolute output file and ignore working dir', async () => {
+    const absolutePath = path.join(os.tmpdir(), 'dev', 'file.yaml');
+    const output = absolutePath;
+    const contents = 'contents';
+    const workingDir = 'working/dir';
+
+    const promise = writeFileWithCliOptions(output, contents, workingDir);
+    await expect(promise).resolves.toBe(absolutePath);
+  });
+
   it('should write to output file under working dir', async () => {
     const output = 'file.yaml';
     const contents = 'contents';
diff --git a/packages/insomnia-inso/src/commands/__tests__/generate-config.test.js b/packages/insomnia-inso/src/commands/__tests__/generate-config.test.js
index e08e0821c4..1cc48eb4fd 100644
--- a/packages/insomnia-inso/src/commands/__tests__/generate-config.test.js
+++ b/packages/insomnia-inso/src/commands/__tests__/generate-config.test.js
@@ -6,6 +6,7 @@ import { writeFileWithCliOptions } from '../../write-file';
 import { globalBeforeAll, globalBeforeEach } from '../../../__jest__/before';
 import logger from '../../logger';
 import { InsoError } from '../../errors';
+import os from 'os';
 
 jest.mock('openapi-2-kong');
 jest.mock('../../write-file');
@@ -120,6 +121,27 @@ describe('generateConfig()', () => {
     expect(logger.__getLogs().log).toEqual([`Configuration generated to "${outputPath}".`]);
   });
 
+  it('should generate documents using absolute path', async () => {
+    mock(o2k.generate).mockResolvedValue({ documents: ['a', 'b'] });
+    const outputPath = 'this-is-the-output-path';
+    mock(writeFileWithCliOptions).mockResolvedValue(outputPath);
+
+    const absolutePath = path.join(os.tmpdir(), 'dev', 'file.yaml');
+
+    const result = await generateConfig(absolutePath, {
+      type: 'kubernetes',
+      workingDir: 'test/dir',
+      output: 'output.yaml',
+    });
+
+    expect(result).toBe(true);
+
+    // Read from workingDir
+    expect(o2k.generate).toHaveBeenCalledWith(absolutePath, ConversionTypeMap.kubernetes);
+
+    expect(logger.__getLogs().log).toEqual([`Configuration generated to "${outputPath}".`]);
+  });
+
   it('should throw InsoError if there is an error thrown by openapi-2-kong', async () => {
     const error = new Error('err');
     mock(o2k.generate).mockRejectedValue(error);
diff --git a/packages/insomnia-inso/src/commands/generate-config.js b/packages/insomnia-inso/src/commands/generate-config.js
index 1319296086..7659399e12 100644
--- a/packages/insomnia-inso/src/commands/generate-config.js
+++ b/packages/insomnia-inso/src/commands/generate-config.js
@@ -52,7 +52,9 @@ export async function generateConfig(
       result = await o2k.generateFromString(specFromDb.contents, ConversionTypeMap[type]);
     } else if (identifier) {
       // try load as a file
-      const fileName = path.join(workingDir || '.', identifier);
+      const fileName = path.isAbsolute(identifier)
+        ? identifier
+        : path.join(workingDir || '.', identifier);
       logger.trace(`Generating config from file \`${fileName}\``);
       result = await o2k.generate(fileName, ConversionTypeMap[type]);
     }
diff --git a/packages/insomnia-inso/src/write-file.js b/packages/insomnia-inso/src/write-file.js
index bcee3294be..65613aa3ae 100644
--- a/packages/insomnia-inso/src/write-file.js
+++ b/packages/insomnia-inso/src/write-file.js
@@ -9,7 +9,7 @@ export async function writeFileWithCliOptions(
   contents: string,
   workingDir?: string,
 ): Promise<string> {
-  const outputPath = path.join(workingDir || '.', output);
+  const outputPath = path.isAbsolute(output) ? output : path.join(workingDir || '.', output);
   try {
     await mkdirp.sync(path.dirname(outputPath));
     await fs.promises.writeFile(outputPath, contents);