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Improve UX around certificate errors #118

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Aug 9, 2023
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18 changes: 18 additions & 0 deletions fixtures/chain-intermediate.crt
Original file line number Diff line number Diff line change
@@ -0,0 +1,18 @@
-----BEGIN CERTIFICATE-----
MIIC/DCCAeSgAwIBAgICEAAwDQYJKoZIhvcNAQELBQAwFDESMBAGA1UEAwwJVEVT
VC1yb290MB4XDTIzMDgwMTAxNDUxM1oXDTI0MDczMTAxNDUxM1owHDEaMBgGA1UE
AwwRVEVTVC1pbnRlcm1lZGlhdGUwggEiMA0GCSqGSIb3DQEBAQUAA4IBDwAwggEK
AoIBAQDYpxiPSJIcdHoDlt6fueRkX8zBC5u9aItDrStM6/VGQRM/NmeAWB/ek1pU
749TaPUAcx5uoMaP2FKqnUN9sExslD5cLY5c/ixAfxBw6dLL3oYHB5vgwr5YUyS2
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XPM8jb/VBXpgW7wA7vMRoewvXLG4xITbh+HXKhDh1n+KLAJLSB4uBrmbmx1/pgpM
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sP5rr7FbAZLGSHx0h9hzav3XuWRv7+mn1m9QplsvaJV2EehiY92C0JmNHt9BvMcX
XTWGWgXMVeacm/0W+3XmQWtltDnBQq8fUsEy0Uts6fJdD/5tEmvYfwEtpomxdFds
-----END CERTIFICATE-----
28 changes: 28 additions & 0 deletions fixtures/chain-intermediate.key
Original file line number Diff line number Diff line change
@@ -0,0 +1,28 @@
-----BEGIN PRIVATE KEY-----
MIIEvAIBADANBgkqhkiG9w0BAQEFAASCBKYwggSiAgEAAoIBAQDYpxiPSJIcdHoD
lt6fueRkX8zBC5u9aItDrStM6/VGQRM/NmeAWB/ek1pU749TaPUAcx5uoMaP2FKq
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F1SDXNNKT6Wg/XNKG9Pdow==
-----END PRIVATE KEY-----
20 changes: 20 additions & 0 deletions fixtures/chain-leaf.crt
Original file line number Diff line number Diff line change
@@ -0,0 +1,20 @@
-----BEGIN CERTIFICATE-----
MIIDMjCCAhqgAwIBAgICEAAwDQYJKoZIhvcNAQELBQAwHDEaMBgGA1UEAwwRVEVT
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395vKvYI
-----END CERTIFICATE-----
28 changes: 28 additions & 0 deletions fixtures/chain-leaf.key
Original file line number Diff line number Diff line change
@@ -0,0 +1,28 @@
-----BEGIN PRIVATE KEY-----
MIIEvAIBADANBgkqhkiG9w0BAQEFAASCBKYwggSiAgEAAoIBAQCiLsCk5U0Xb0VS
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i45lVy8xNJU85Fmzex0B0g==
-----END PRIVATE KEY-----
18 changes: 18 additions & 0 deletions fixtures/chain-root.crt
Original file line number Diff line number Diff line change
@@ -0,0 +1,18 @@
-----BEGIN CERTIFICATE-----
MIIC5TCCAc2gAwIBAgIUXtcOjsFS175nGr07+htPEPGe2bYwDQYJKoZIhvcNAQEL
BQAwFDESMBAGA1UEAwwJVEVTVC1yb290MB4XDTIzMDgwMTAxNDUxM1oXDTMzMDcy
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-----END CERTIFICATE-----
28 changes: 28 additions & 0 deletions fixtures/chain-root.key
Original file line number Diff line number Diff line change
@@ -0,0 +1,28 @@
-----BEGIN PRIVATE KEY-----
MIIEvgIBADANBgkqhkiG9w0BAQEFAASCBKgwggSkAgEAAoIBAQDVyB+pQ0g/Qvfn
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h/z2c6S/DifigZ5sYSyL4TqJ
-----END PRIVATE KEY-----
56 changes: 56 additions & 0 deletions fixtures/chain.crt
Original file line number Diff line number Diff line change
@@ -0,0 +1,56 @@
-----BEGIN CERTIFICATE-----
MIIDMjCCAhqgAwIBAgICEAAwDQYJKoZIhvcNAQELBQAwHDEaMBgGA1UEAwwRVEVT
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395vKvYI
-----END CERTIFICATE-----
-----BEGIN CERTIFICATE-----
MIIC/DCCAeSgAwIBAgICEAAwDQYJKoZIhvcNAQELBQAwFDESMBAGA1UEAwwJVEVT
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ZwfysAIt6DjRylEIMA0GCSqGSIb3DQEBCwUAA4IBAQB00UMFcTDyDUidWamh/fzS
Z6pv2ms0mKHXeVYdqUGtWPjl9uocWGJXdgD3C77Ifpx02zayhtpdfSvvajyEnTAd
XPM8jb/VBXpgW7wA7vMRoewvXLG4xITbh+HXKhDh1n+KLAJLSB4uBrmbmx1/pgpM
rXJPAGv4ARzkozcs98qWND3dWAjDNn+7Wxb0wVhcYgrmvyQyNAUdgYImxZSqn7rR
sP5rr7FbAZLGSHx0h9hzav3XuWRv7+mn1m9QplsvaJV2EehiY92C0JmNHt9BvMcX
XTWGWgXMVeacm/0W+3XmQWtltDnBQq8fUsEy0Uts6fJdD/5tEmvYfwEtpomxdFds
-----END CERTIFICATE-----
-----BEGIN CERTIFICATE-----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-----END CERTIFICATE-----
28 changes: 28 additions & 0 deletions fixtures/chain.key
Original file line number Diff line number Diff line change
@@ -0,0 +1,28 @@
-----BEGIN PRIVATE KEY-----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-----END PRIVATE KEY-----
134 changes: 134 additions & 0 deletions fixtures/generate.bash
Original file line number Diff line number Diff line change
@@ -0,0 +1,134 @@
#!/usr/bin/env bash

set -xeuo pipefail

function prepare() {
local cwd=$1
local fwd=$(readlink -f "$cwd")
mkdir -p "$cwd"/{certs,crl,newcerts,private}
echo 1000 > "$cwd/serial"
touch "$cwd"/{index.txt,index.txt.attr}

echo '
[ ca ]
default_ca = CA_default
[ CA_default ]
dir = '"$fwd"'
certs = $dir/certs # Where the issued certs are kept
crl_dir = $dir/crl # Where the issued crl are kept
database = $dir/index.txt # database index file.
new_certs_dir = $dir/newcerts # default place for new certs.
certificate = $dir/cacert.pem # The CA certificate
serial = $dir/serial # The current serial number
crl = $dir/crl.pem # The current CRL
private_key = $dir/private/ca.key.pem # The private key
RANDFILE = $dir/.rnd # private random number file
nameopt = default_ca
certopt = default_ca
policy = policy_match
default_days = 365
default_md = sha256

[ policy_match ]
countryName = optional
stateOrProvinceName = optional
organizationName = optional
organizationalUnitName = optional
commonName = supplied
emailAddress = optional

[req]
req_extensions = v3_req
distinguished_name = req_distinguished_name

[req_distinguished_name]

[v3_req]' > "$cwd/openssl.cnf"

if [[ $cwd == out ]] ; then
echo "keyUsage = digitalSignature, keyEncipherment" >> "$cwd/openssl.cnf"
echo "extendedKeyUsage = serverAuth, clientAuth" >> "$cwd/openssl.cnf"
echo "subjectAltName = DNS:localhost" >> "$cwd/openssl.cnf"
else
echo "basicConstraints = CA:TRUE" >> "$cwd/openssl.cnf"
fi
}

# chain generates three certificates in a chain.
function chain() {
rm {root,intermediate,out} -rf
prepare root
prepare intermediate
prepare out

# Create root certificate and key.
openssl genrsa -out root/private/ca.key 2048
openssl req -new -x509 -sha256 -days 3650 \
-config root/openssl.cnf -extensions v3_req \
-key root/private/ca.key --out root/certs/ca.crt \
-subj '/CN=TEST-root'

# Create intermediate key and request.
openssl genrsa -out intermediate/private/intermediate.key 2048
openssl req -new -sha256 \
-config intermediate/openssl.cnf -extensions v3_req \
-key intermediate/private/intermediate.key -out intermediate/certs/intermediate.csr \
-subj '/CN=TEST-intermediate'

# Sign intermediate request with root to create a cert.
openssl ca -batch -notext -md sha256 \
-config intermediate/openssl.cnf -extensions v3_req \
-keyfile root/private/ca.key -cert root/certs/ca.crt \
-in intermediate/certs/intermediate.csr \
-out intermediate/certs/intermediate.crt

# Create a key and request for an end certificate.
openssl req -new -days 365 -nodes -newkey rsa:2048 \
-config out/openssl.cnf -extensions v3_req \
-keyout out/private/localhost.key -out out/certs/localhost.csr \
-subj "/CN=localhost"

# Sign that with the intermediate.
openssl ca -batch \
-config out/openssl.cnf -extensions v3_req \
-keyfile intermediate/private/intermediate.key -cert intermediate/certs/intermediate.crt \
-out out/certs/localhost.crt \
-infiles out/certs/localhost.csr

mv out/certs/localhost.crt chain-leaf.crt
mv out/private/localhost.key chain-leaf.key
mv intermediate/certs/intermediate.crt chain-intermediate.crt
mv intermediate/private/intermediate.key chain-intermediate.key
mv root/certs/ca.crt chain-root.crt
mv root/private/ca.key chain-root.key

rm {out,intermediate,root} -r

cat chain-leaf.crt chain-intermediate.crt chain-root.crt > chain.crt
cp chain-leaf.key chain.key
}

# non-signing generates a self-signed certificate that has cert signing
# explicitly omitted.
function non-signing() {
openssl req -x509 -nodes -newkey rsa:2048 \
-keyout no-signing.key -out no-signing.crt \
-addext "keyUsage = digitalSignature, keyEncipherment" \
-addext "subjectAltName=DNS:localhost" \
-subj "/CN=localhost"
}

# self-signed generates a certificate without specifying key usage.
function self-signed() {
openssl req -x509 -nodes -newkey rsa:2048 \
-keyout self-signed.key -out self-signed.crt \
-addext "subjectAltName=DNS:localhost" \
-subj "/CN=localhost"
}

function main() {
local name=$1 ; shift
"$name" "$@"
}

main "$@"
19 changes: 19 additions & 0 deletions fixtures/no-signing.crt
Original file line number Diff line number Diff line change
@@ -0,0 +1,19 @@
-----BEGIN CERTIFICATE-----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-----END CERTIFICATE-----
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