diff --git a/cmds/swagger.js b/cmds/swagger.js
index 52a336d44..7506dcc31 100644
--- a/cmds/swagger.js
+++ b/cmds/swagger.js
@@ -44,6 +44,7 @@ exports.run = async function(opts) {
   const { spec, version } = opts;
   let { key, id } = opts;
   let selectedVersion;
+  let isUpdate;
 
   if (!key && opts.token) {
     console.warn(
@@ -56,9 +57,9 @@ exports.run = async function(opts) {
     return Promise.reject(new Error('No project API key provided. Please use `--key`.'));
   }
 
-  function callApi(specPath, versionCleaned) {
+  async function callApi(specPath, versionCleaned) {
     function success(data) {
-      const message = !id
+      const message = !isUpdate
         ? "You've successfully uploaded a new swagger file to your ReadMe project!"
         : "You've successfully updated a swagger file on your ReadMe project!";
       console.log(`
@@ -99,15 +100,46 @@ exports.run = async function(opts) {
       resolveWithFullResponse: true,
     };
 
-    // Create
-    if (!id) {
+    function createSpec() {
       return request.post(`${config.host}/api/v1/api-specification`, options).then(success, error);
     }
 
-    // Update
-    return request
-      .put(`${config.host}/api/v1/api-specification/${id}`, options)
-      .then(success, error);
+    function updateSpec(specId) {
+      isUpdate = true;
+
+      return request
+        .put(`${config.host}/api/v1/api-specification/${specId}`, options)
+        .then(success, error);
+    }
+
+    /*
+      Create a new OAS file in Readme:
+        - Enter flow if user does not pass an id as cli arg
+        - Check to see if any existing files exist with a specific version
+        - If none exist, default to creating a new instance of a spec
+        - If found, prompt user to either create a new spec or update an existing one
+    */
+
+    if (!id) {
+      const apiSettings = await request.get(`${config.host}/api/v1/api-specification`, {
+        headers: {
+          'x-readme-version': versionCleaned,
+        },
+        json: true,
+        auth: { user: key },
+      });
+
+      if (!apiSettings.length) return createSpec();
+
+      const { option, specId } = await prompt(promptOpts.createOasPrompt(apiSettings));
+      return option === 'create' ? createSpec() : updateSpec(specId);
+    }
+
+    /*
+      Update an existing OAS file in Readme:
+        - Enter flow if user passes an id as cli arg
+    */
+    return updateSpec(id);
   }
 
   async function getSwaggerVersion(versionFlag) {
diff --git a/lib/prompts.js b/lib/prompts.js
index 05b685e2f..88312c5f8 100644
--- a/lib/prompts.js
+++ b/lib/prompts.js
@@ -36,6 +36,32 @@ exports.generatePrompts = versionList => [
   },
 ];
 
+exports.createOasPrompt = specList => [
+  {
+    type: 'select',
+    name: 'option',
+    message: 'Would you like to update an existing OAS file or create a new one?',
+    choices: [
+      { message: 'Update existing', value: 'update' },
+      { message: 'Create a new spec', value: 'create' },
+    ],
+  },
+  {
+    type: 'select',
+    name: 'specId',
+    message: 'Select your desired file to update',
+    skip() {
+      return this.enquirer.answers.option !== 'update';
+    },
+    choices: specList.map(s => {
+      return {
+        message: s.title,
+        value: s._id, // eslint-disable-line no-underscore-dangle
+      };
+    }),
+  },
+];
+
 exports.createVersionPrompt = (versionList, opts, isUpdate) => [
   {
     type: 'select',
diff --git a/test/cmds/swagger.test.js b/test/cmds/swagger.test.js
index 686e0f866..15024dd31 100644
--- a/test/cmds/swagger.test.js
+++ b/test/cmds/swagger.test.js
@@ -14,6 +14,8 @@ describe('rdme swagger', () => {
   afterEach(() => nock.cleanAll());
 
   it('should POST a discovered file if none provided', () => {
+    promptHandler.createOasPrompt.mockResolvedValue({ option: 'create' });
+
     const mock = nock(config.host)
       .get(`/api/v1/version`)
       .basicAuth({ user: key })
@@ -21,6 +23,9 @@ describe('rdme swagger', () => {
       .post('/api/v1/version')
       .basicAuth({ user: key })
       .reply(200, { from: '1.0.1', version: '1.0.1' })
+      .get(`/api/v1/api-specification`)
+      .basicAuth({ user: key })
+      .reply(200, [])
       .post('/api/v1/api-specification', body => body.match('form-data; name="spec"'))
       .delayConnection(1000)
       .basicAuth({ user: key })
@@ -42,6 +47,9 @@ describe('rdme swagger', () => {
       .get(`/api/v1/version/${version}`)
       .basicAuth({ user: key })
       .reply(200, { version: '1.0.0' })
+      .get(`/api/v1/api-specification`)
+      .basicAuth({ user: key })
+      .reply(200, [])
       .post('/api/v1/api-specification', body => body.match('form-data; name="spec"'))
       .delayConnection(1000)
       .basicAuth({ user: key })
@@ -54,6 +62,9 @@ describe('rdme swagger', () => {
 
   it('should POST to the swagger api if no id provided', () => {
     const mock = nock(config.host)
+      .get(`/api/v1/api-specification`)
+      .basicAuth({ user: key })
+      .reply(200, [])
       .get(`/api/v1/version/${version}`)
       .basicAuth({ user: key })
       .reply(200, { version: '1.0.0' })
@@ -71,6 +82,9 @@ describe('rdme swagger', () => {
       .get(`/api/v1/version/${version}`)
       .basicAuth({ user: key })
       .reply(200, { version: '1.0.0' })
+      .get(`/api/v1/api-specification`)
+      .basicAuth({ user: key })
+      .reply(200, [])
       .post('/api/v1/api-specification', body => body.match('form-data; name="spec"'))
       .delayConnection(1000)
       .basicAuth({ user: key })
@@ -98,6 +112,9 @@ describe('rdme swagger', () => {
       .post('/api/v1/version')
       .basicAuth({ user: key })
       .reply(200, { from: '1.0.1', version: '1.0.1' })
+      .get(`/api/v1/api-specification`)
+      .basicAuth({ user: key })
+      .reply(200, [])
       .post('/api/v1/api-specification', body => body.match('form-data; name="spec"'))
       .basicAuth({ user: key })
       .reply(201, { id: 1 });
diff --git a/test/lib/prompts.test.js b/test/lib/prompts.test.js
index f6f1cfe30..1d6030364 100644
--- a/test/lib/prompts.test.js
+++ b/test/lib/prompts.test.js
@@ -11,6 +11,17 @@ const versionlist = [
   },
 ];
 
+const specList = [
+  {
+    _id: 'spec1',
+    title: 'spec1_title',
+  },
+  {
+    _id: 'spec2',
+    title: 'spec2_title',
+  },
+];
+
 describe('prompt test bed', () => {
   let enquirer;
 
@@ -53,6 +64,32 @@ describe('prompt test bed', () => {
     });
   });
 
+  describe('createOasPrompt()', () => {
+    it('should return a create option if selected', async () => {
+      enquirer.on('prompt', async prompt => {
+        await prompt.keypress(null, { name: 'down' });
+        await prompt.submit();
+      });
+      const answer = await enquirer.prompt(promptHandler.createOasPrompt([{}]));
+
+      assert.equal(answer.option, 'create');
+      assert.equal(answer.specId, '');
+    });
+
+    it('should return specId if user chooses to update file', async () => {
+      enquirer.on('prompt', async prompt => {
+        await prompt.keypress(null, { name: 'down' });
+        await prompt.keypress(null, { name: 'up' });
+        await prompt.submit();
+        await prompt.submit();
+      });
+      const answer = await enquirer.prompt(promptHandler.createOasPrompt(specList));
+
+      assert.equal(answer.option, 'update');
+      assert.equal(answer.specId, 'spec1');
+    });
+  });
+
   describe('createVersionPrompt()', () => {
     it('should allow user to choose a fork if flag is not passed', async () => {
       const opts = { main: true, beta: true };