diff --git a/packages/cli/src/util/deploy/process-deployment.ts b/packages/cli/src/util/deploy/process-deployment.ts
index 3c001d228..56e01b0fe 100644
--- a/packages/cli/src/util/deploy/process-deployment.ts
+++ b/packages/cli/src/util/deploy/process-deployment.ts
@@ -115,29 +115,39 @@ export default async function processDeployment({
           .reduce((a: number, b: number) => a + b, 0);
         const totalSizeHuman = bytes.format(missingSize, { decimalPlaces: 1 });
 
-        uploads.forEach((e: any) =>
-          e.on('progress', () => {
-            const uploadedBytes = uploads.reduce((acc: number, e: any) => {
-              return acc + e.bytesUploaded;
-            }, 0);
+        // When stderr is not a TTY then we only want to
+        // print upload progress in 25% increments
+        let nextStep = 0;
+        const stepSize = now._client.stderr.isTTY ? 0 : 0.25;
 
-            const bar = progress(uploadedBytes, missingSize);
-            if (!bar || uploadedBytes === missingSize) {
-              output.spinner(deployingSpinnerVal, 0);
-            } else {
-              const uploadedHuman = bytes.format(uploadedBytes, {
-                decimalPlaces: 1,
-                fixedDecimals: true,
-              });
+        const updateProgress = () => {
+          const uploadedBytes = uploads.reduce((acc: number, e: any) => {
+            return acc + e.bytesUploaded;
+          }, 0);
+
+          const bar = progress(uploadedBytes, missingSize);
+          if (!bar) {
+            output.spinner(deployingSpinnerVal, 0);
+          } else {
+            const uploadedHuman = bytes.format(uploadedBytes, {
+              decimalPlaces: 1,
+              fixedDecimals: true,
+            });
+            const percent = uploadedBytes / missingSize;
+            if (percent >= nextStep) {
               output.spinner(
                 `Uploading ${chalk.reset(
                   `[${bar}] (${uploadedHuman}/${totalSizeHuman})`
                 )}`,
                 0
               );
+              nextStep += stepSize;
             }
-          })
-        );
+          }
+        };
+
+        uploads.forEach((e: any) => e.on('progress', updateProgress));
+        updateProgress();
       }
 
       if (event.type === 'file-uploaded') {
diff --git a/packages/cli/test/unit/commands/deploy.test.ts b/packages/cli/test/unit/commands/deploy.test.ts
index 3266288f1..5bbaeeb81 100644
--- a/packages/cli/test/unit/commands/deploy.test.ts
+++ b/packages/cli/test/unit/commands/deploy.test.ts
@@ -1,4 +1,7 @@
+import bytes from 'bytes';
+import fs from 'fs-extra';
 import { join } from 'path';
+import { randomBytes } from 'crypto';
 import { fileNameSymbol } from '@vercel/client';
 import { client } from '../../mocks/client';
 import deploy from '../../../src/commands/deploy';
@@ -199,4 +202,119 @@ describe('deploy', () => {
       process.chdir(originalCwd);
     }
   });
+
+  it('should upload missing files', async () => {
+    const cwd = setupFixture('commands/deploy/archive');
+    const originalCwd = process.cwd();
+
+    // Add random 1mb file
+    await fs.writeFile(join(cwd, 'data'), randomBytes(bytes('1mb')));
+
+    try {
+      process.chdir(cwd);
+
+      const user = useUser();
+      useTeams('team_dummy');
+      useProject({
+        ...defaultProject,
+        name: 'archive',
+        id: 'archive',
+      });
+
+      let body: any;
+      let fileUploaded = false;
+      client.scenario.post(`/v13/deployments`, (req, res) => {
+        if (fileUploaded) {
+          body = req.body;
+          res.json({
+            creator: {
+              uid: user.id,
+              username: user.username,
+            },
+            id: 'dpl_archive_test',
+          });
+        } else {
+          const sha = req.body.files[0].sha;
+          res.status(400).json({
+            error: {
+              code: 'missing_files',
+              message: 'Missing files',
+              missing: [sha],
+            },
+          });
+        }
+      });
+      client.scenario.post('/v2/files', (req, res) => {
+        // Wait for file to be finished uploading
+        req.on('data', () => {
+          // Noop
+        });
+        req.on('end', () => {
+          fileUploaded = true;
+          res.end();
+        });
+      });
+      client.scenario.get(`/v13/deployments/dpl_archive_test`, (req, res) => {
+        res.json({
+          creator: {
+            uid: user.id,
+            username: user.username,
+          },
+          id: 'dpl_archive_test',
+          readyState: 'READY',
+          aliasAssigned: true,
+          alias: [],
+        });
+      });
+      client.scenario.get(
+        `/v10/now/deployments/dpl_archive_test`,
+        (req, res) => {
+          res.json({
+            creator: {
+              uid: user.id,
+              username: user.username,
+            },
+            id: 'dpl_archive_test',
+            readyState: 'READY',
+            aliasAssigned: true,
+            alias: [],
+          });
+        }
+      );
+
+      // When stderr is not a TTY we expect 5 progress lines to be printed
+      client.stderr.isTTY = false;
+
+      client.setArgv('deploy', '--archive=tgz');
+      const uploadingLines: string[] = [];
+      client.stderr.on('data', data => {
+        if (data.startsWith('Uploading [')) {
+          uploadingLines.push(data);
+        }
+      });
+      client.stderr.resume();
+      const exitCode = await deploy(client);
+      expect(exitCode).toEqual(0);
+      expect(body?.files?.length).toEqual(1);
+      expect(body?.files?.[0].file).toEqual('.vercel/source.tgz');
+      expect(uploadingLines.length).toEqual(5);
+      expect(
+        uploadingLines[0].startsWith('Uploading [--------------------]')
+      ).toEqual(true);
+      expect(
+        uploadingLines[1].startsWith('Uploading [=====---------------]')
+      ).toEqual(true);
+      expect(
+        uploadingLines[2].startsWith('Uploading [==========----------]')
+      ).toEqual(true);
+      expect(
+        uploadingLines[3].startsWith('Uploading [===============-----]')
+      ).toEqual(true);
+      expect(
+        uploadingLines[4].startsWith('Uploading [====================]')
+      ).toEqual(true);
+    } finally {
+      process.chdir(originalCwd);
+    }
+  });
 });
diff --git a/packages/client/src/upload.ts b/packages/client/src/upload.ts
index a12441aaa..25c8a0d15 100644
--- a/packages/client/src/upload.ts
+++ b/packages/client/src/upload.ts
@@ -1,4 +1,5 @@
-import { Agent } from 'https';
+import http from 'http';
+import https from 'https';
 import { Readable } from 'stream';
 import { EventEmitter } from 'events';
 import retry from 'async-retry';
@@ -78,7 +79,9 @@ export async function* upload(
   debug('Building an upload list...');
 
   const semaphore = new Sema(50, { capacity: 50 });
-  const agent = new Agent({ keepAlive: true });
+  const agent = apiUrl?.startsWith('https://')
+    ? new https.Agent({ keepAlive: true })
+    : new http.Agent({ keepAlive: true });
 
   shas.forEach((sha, index) => {
     const uploadProgress = uploads[index];