This pull request makes the IMAP and SMTP encryption setting actually
honor what the user selects.
As per spec there's 3 modes: SSL/TLS (implicit TLS from the start),
STARTTLS (it will attempt TLS but if the server doesn't support it, it
gracefully falls back to plaintext), NONE (plaintext)
Current implementation had a boolean flag for this, this replaces it
with the 3 modes
Upgrade command to migrate all existing accounts, to not risk breaking
anyone's existing account in production we map each account to the mode
that matches its current behavior, so nothing changes on the wire
/closes #21300
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---------
Co-authored-by: Charles Bochet <charles@twenty.com>
## Summary
closes https://github.com/twentyhq/core-team-issues/issues/2464
Introduces compile-time branded types to distinguish encrypted
ciphertext from plaintext strings, preventing mix-ups like the one fixed
in #20819 — but at the type level rather in addition to the one existing
at runtime.
### Branded string primitives
- Created `EncryptedString` and `PlaintextString` as hard nominal brands
using `z.string().brand(...)`, making them non-assignable to each other
or to raw `string`
- Created `isEncryptedString` type predicate to narrow `string` to
`EncryptedString` based on the `enc:v2:` envelope prefix
- Retyped `SecretEncryptionService`: `encryptVersioned` accepts
`PlaintextString`, `decryptVersioned` returns `PlaintextString`
### Entity typing
- Typed encrypted columns across entities:
`SigningKeyEntity.privateKey`,
`TwoFactorAuthenticationMethodEntity.secret`,
`ApplicationRegistrationVariableEntity.encryptedValue`,
`ApplicationVariableEntity.value`
- Parameterized JSONB types for connected account connection parameters
(`ImapSmtpCaldavParams<Pwd>`) with reusable aliases
`EncryptedImapSmtpCaldavParams` / `DecryptedImapSmtpCaldavParams`
- Typed DTOs (`CreateApplicationRegistrationVariableInput`,
`UpdateApplicationRegistrationVariablePayload`,
`UpdateApplicationVariableEntityInput`) with `PlaintextString`
### ApplicationVariable always-encrypt uniformization
- Retyped `ApplicationVariableEntity.value` to `EncryptedString | ''` —
all values are now encrypted regardless of `isSecret`
- Updated `ApplicationVariableEntityService` to always encrypt on write
and always decrypt on read
- Simplified `UpdateApplicationVariableActionHandlerService` by removing
conditional encrypt/decrypt-on-isSecret-toggle logic
- Added slow instance command (`2.9.0`) to backfill-encrypt existing
`isSecret=false` plaintext rows and tighten the `CHECK` constraint
### ConfigStorageService refactor
- Split `convertAndSecureValue` (which used `any`) into two well-typed
methods: `convertAndDecrypt` and `convertAndEncrypt`
- Introduced `isSensitiveStringValue` type predicate to narrow values
before encryption/decryption
### What's next
- Typeorm entity derivation to strictly type sitemap configuration as
code + handler logic for encryption rotation
- https://github.com/twentyhq/core-team-issues/issues/2465
## Summary
Adds a new `connected-account-connection-parameters` site to the
`secret-encryption:rotate` CLI introduced in #20613, so the nested
password envelopes inside `connectedAccount.connectionParameters` (IMAP
/ SMTP / CALDAV — encrypted at-rest in #20673) are re-encrypted under
the current `ENCRYPTION_KEY` alongside every other at-rest secret site.
Without this, rotating `ENCRYPTION_KEY` on a 2.7+ instance would
silently leave IMAP / SMTP / CalDav passwords on the old key id.
### Why a new handler
A dedicated handler is required (rather than reusing
`ColumnRotationSiteHandler`) because the envelope lives at
`connectionParameters->'<PROTOCOL>'->>'password'`, not in the whole
column, and up to three independent envelopes may need rotating per row.
The handler:
- Uses the same cursor-based, idempotent, online pattern as the existing
handlers, with a SQL predicate that skips rows where every non-null
protocol password is already on the current key id.
- Threads \`workspaceId\` into HKDF, matching how
\`EncryptConnectionParametersSlowInstanceCommand\` backfilled.
- Rebuilds only the protocols whose passwords are not yet current, so a
partial mid-row failure cannot cause unnecessary re-encryption on
resume.
- Guards the UPDATE with jsonb-level deep equality (\`IS NOT DISTINCT
FROM CAST(:json AS jsonb)\`) so optimistic concurrency is unaffected by
Postgres's internal jsonb key ordering vs. JSON.stringify ordering.
- Refuses to rotate plaintext passwords (counted as \`errors\`) —
operators must finish the 2.7 slow instance command
(\`EncryptConnectionParametersSlowInstanceCommand\`) before running
rotation.
### Sites covered (now)
| Site | Location | Scope |
| --- | --- | --- |
| \`connected-account-access-token\` | \`connectedAccount.accessToken\`
| workspace |
| \`connected-account-refresh-token\` |
\`connectedAccount.refreshToken\` | workspace |
| **\`connected-account-connection-parameters\`** (new) |
\`connectedAccount.connectionParameters.{IMAP,SMTP,CALDAV}.password\` |
workspace |
| \`application-variable\` | \`applicationVariable.value\` (isSecret) |
workspace |
| \`application-registration-variable\` |
\`applicationRegistrationVariable.encryptedValue\` | instance |
| \`signing-key-private-key\` | \`signingKey.privateKey\` | instance |
| \`totp-secret\` | \`twoFactorAuthenticationMethod.secret\` | workspace
|
| \`sensitive-config-storage\` | \`keyValuePair.value\` (sensitive
STRING configs) | instance |
Paul Rastoin
