# Debian 11 apt HTTPS upgrade

> Step-by-step guidance for upgrading legacy TLS clients and servers while filtering outbound traffic with DiscrimiNAT OTF.

Upgrading package downloads from HTTP to HTTPS can help with meeting standards such as PCI DSS and NIST SP 800-53. Use of secure transport can also mitigate against future zero-day, remote code vulnerabilities with package managers themselves, such as [CVE-2019-3462](https://security-tracker.debian.org/tracker/CVE-2019-3462), [CVE-2016-1252](https://security-tracker.debian.org/tracker/CVE-2016-1252) and [CVE-2014-6273](https://security-tracker.debian.org/tracker/CVE-2014-6273) in the past.

This short guide aims to help in upgrading the default repositories' URLs from plaintext to encrypted.

## Virtual Machine

The commands simply change the URL scheme from `http` to `https`, making a backup file (with extension _.orig_) in the process.

### AWS User Data

```bash
#!/bin/bash -ex
sed --in-place=.orig --regexp-extended 's%http://(cdn-aws.)*(deb|security).debian.org%https://\2.debian.org%g' /etc/apt/sources.list
```

### GCP Startup Script

```bash
#!/bin/bash -ex
sed --in-place=.orig --regexp-extended 's%http://(deb|security).debian.org%https://\1.debian.org%g' /etc/apt/sources.list
sed --in-place=.orig --regexp-extended 's%http://packages.cloud.google.com%https://packages.cloud.google.com%g' /etc/apt/sources.list.d/*.list
```

## Container

### Dockerfile

```Dockerfile
FROM debian:11-slim

RUN echo 'Acquire::https::Verify-Peer "false";' > /etc/apt/apt.conf.d/99_tmp_ssl-verify-off.conf && \
    sed --in-place=.orig --regexp-extended 's%http://(deb|security).debian.org%https://\1.debian.org%g' /etc/apt/sources.list && \
    apt-get update && \
    apt-get install --assume-yes ca-certificates && \
    rm /etc/apt/apt.conf.d/99_tmp_ssl-verify-off.conf
```

These commands first turn off SSL certificate verification because (a) the container build process may be behind [DiscrimiNAT](/discriminat/) already and (b) the CA certificates bundle needs to be downloaded for the verification process to work. [DiscrimiNAT](/discriminat/) independently verifies each connection and will ensure _apt_ connected to the CDN specified in spite of not verifying the certificate. The configuration that turned the verification off is removed after the bundle is installed.

## Allowlist

### FQDNs

```
deb.debian.org,security.debian.org,packages.cloud.google.com
```

### DiscrimiNAT Annotation

```
discriminat:tls:deb.debian.org,security.debian.org,packages.cloud.google.com
```