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feat: add SMTP auth & TLS support #13902

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Merged
merged 14 commits into from
Jul 19, 2024
Merged

feat: add SMTP auth & TLS support #13902

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566a484
WIP: SMTP tests
dannykopping Jul 12, 2024
ab11cc1
WIP: TLS tests
dannykopping Jul 15, 2024
379cf22
Flags
dannykopping Jul 16, 2024
cf93129
Self-review
dannykopping Jul 16, 2024
e987643
make lint/fmt
dannykopping Jul 16, 2024
ea318cc
Ignore typo in HELO
dannykopping Jul 16, 2024
5ecfe4a
make update-flake / make update-golden-files
dannykopping Jul 16, 2024
01d4f2f
make lint / make gen
dannykopping Jul 16, 2024
6e34de6
Make tests more resilient across platforms
dannykopping Jul 16, 2024
598c9bb
Wait for server
dannykopping Jul 16, 2024
8baa141
Review comments
dannykopping Jul 18, 2024
60cb30a
make gen
dannykopping Jul 18, 2024
4f7a910
Using hosted image URL rather than SVG since many clients do not supp…
dannykopping Jul 18, 2024
5a8331f
Reference image hosted on coder.com instead
dannykopping Jul 18, 2024
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69 changes: 69 additions & 0 deletions coderd/apidoc/docs.go
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69 changes: 69 additions & 0 deletions coderd/apidoc/swagger.json
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18 changes: 18 additions & 0 deletions coderd/notifications/dispatch/fixtures/ca.conf
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[ req ]
distinguished_name = req_distinguished_name
x509_extensions = v3_ca
prompt = no

[ req_distinguished_name ]
C = ZA
ST = WC
L = Cape Town
O = Coder
OU = Team Coconut
CN = Coder CA

[ v3_ca ]
basicConstraints = critical,CA:TRUE
keyUsage = critical,keyCertSign,cRLSign
subjectKeyIdentifier = hash
authorityKeyIdentifier = keyid:always,issuer:always
25 changes: 25 additions & 0 deletions coderd/notifications/dispatch/fixtures/ca.crt
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-----BEGIN CERTIFICATE-----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==
-----END CERTIFICATE-----
28 changes: 28 additions & 0 deletions coderd/notifications/dispatch/fixtures/ca.key
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-----BEGIN PRIVATE KEY-----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-----END PRIVATE KEY-----
1 change: 1 addition & 0 deletions coderd/notifications/dispatch/fixtures/ca.srl
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0330C6D190E3FE649DAFCDA2F4D765E2D29328DE
90 changes: 90 additions & 0 deletions coderd/notifications/dispatch/fixtures/generate.sh
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#!/bin/bash

# Set filenames
CA_KEY="ca.key"
CA_CERT="ca.crt"
SERVER_KEY="server.key"
SERVER_CSR="server.csr"
SERVER_CERT="server.crt"
CA_CONF="ca.conf"
SERVER_CONF="server.conf"
V3_EXT_CONF="v3_ext.conf"

# Generate the CA key
openssl genpkey -algorithm RSA -out $CA_KEY -pkeyopt rsa_keygen_bits:2048

# Create the CA configuration file
cat >$CA_CONF <<EOL
[ req ]
distinguished_name = req_distinguished_name
x509_extensions = v3_ca
prompt = no

[ req_distinguished_name ]
C = ZA
ST = WC
L = Cape Town
O = Coder
OU = Team Coconut
CN = Coder CA

[ v3_ca ]
basicConstraints = critical,CA:TRUE
keyUsage = critical,keyCertSign,cRLSign
subjectKeyIdentifier = hash
authorityKeyIdentifier = keyid:always,issuer:always
EOL

# Generate the CA certificate
openssl req -new -x509 -key $CA_KEY -out $CA_CERT -days 3650 -config $CA_CONF -extensions v3_ca

# Generate the server key
openssl genpkey -algorithm RSA -out $SERVER_KEY -pkeyopt rsa_keygen_bits:2048

# Create the server configuration file
cat >$SERVER_CONF <<EOL
[ req ]
distinguished_name = req_distinguished_name
req_extensions = v3_req
prompt = no

[ req_distinguished_name ]
C = ZA
ST = WC
L = Cape Town
O = Coder
OU = Team Coconut
CN = myserver.local

[ v3_req ]
subjectAltName = @alt_names

[ alt_names ]
DNS.1 = myserver.local
DNS.2 = www.myserver.local
IP.1 = 127.0.0.1
EOL

# Generate the server CSR
openssl req -new -key $SERVER_KEY -out $SERVER_CSR -config $SERVER_CONF

# Create the server extensions configuration file
cat >$V3_EXT_CONF <<EOL
authorityKeyIdentifier=keyid,issuer
basicConstraints=CA:FALSE
keyUsage = digitalSignature, nonRepudiation, keyEncipherment, dataEncipherment
subjectAltName = @alt_names

[ alt_names ]
DNS.1 = myserver.local
DNS.2 = www.myserver.local
IP.1 = 127.0.0.1
EOL

# Generate the server certificate signed by the CA with a validity of 825 days
openssl x509 -req -in $SERVER_CSR -CA $CA_CERT -CAkey $CA_KEY -CAcreateserial -out $SERVER_CERT -days 825 -extfile $V3_EXT_CONF

# Verify the server certificate
openssl x509 -in $SERVER_CERT -text -noout | grep -A 1 "Subject Alternative Name"

echo "CA and server certificates generated successfully."
1 change: 1 addition & 0 deletions coderd/notifications/dispatch/fixtures/password.txt
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🤫
20 changes: 20 additions & 0 deletions coderd/notifications/dispatch/fixtures/server.conf
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[ req ]
distinguished_name = req_distinguished_name
req_extensions = v3_req
prompt = no

[ req_distinguished_name ]
C = ZA
ST = WC
L = Cape Town
O = Coder
OU = Team Coconut
CN = myserver.local

[ v3_req ]
subjectAltName = @alt_names

[ alt_names ]
DNS.1 = myserver.local
DNS.2 = www.myserver.local
IP.1 = 127.0.0.1
24 changes: 24 additions & 0 deletions coderd/notifications/dispatch/fixtures/server.crt
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-----BEGIN CERTIFICATE-----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-----END CERTIFICATE-----
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