For some, LDAP, just like X.500, is black magic. I won't argue against. Sometimes it really shows surprising behavior. It always makes sense, if you think about what LDAP is built for. One surprising behavior is the handling of the "Insignificant Space"
LDAP supports syntax and comparator methods. The syntax specifies how the entry should look. Usually this is some form of text, but numbers or stuff like telephone numbers are supported as well. The comparators specifies how the values are compared. Most of the text comparators are defined to apply the handling of insignificant spaces.
Insignificant space handling normalizes the use of spaces. First all leading and trailing spaces are removed. All the internal spaces are normalized to at most two spaces. At the end all strings starts and ends with one space to allow proper sub-string matches. The resulting strings are used for comparisons.
This behavior makes sense most of the time. If the user want to find something in the directory, he usually don't cares about spaces, but about content. But I found one occurrence where this produces some grieve.
Postfix supports LDAP since some time. And lets say, it does not care about spaces in its queries. This is no problem as e-mail addresses do not contain spaces. Or do they?
Yes, e-mail addresses can contain spaces. This is not widely known, but still allowed. This addresses are quoted and the command looks like RCPT TO:<"␣test"@example.com>. The local part is quoted and contains a space at the beginning. And this is where the problem starts.
Postfix sanitizes the address. It uses a simplified internal representation of the address for all lookups. So the address gets ␣firstname.lastname@example.org. This form is used in all table lookups.
The LDAP table uses the internal form of the address. This address is copied verbatim into the query. This query may look this way (mail=␣email@example.com). It is sent to the server this way.
The LDAP server applies the insignificant space modifications. The query is now interpreted and the comparator specified modifications are applied. The query gets effectively changed to (firstname.lastname@example.org). And this is where the fun starts.
Postfix accepts undeliverable mails. Depending on the setup, such LDAP queries may be used to check for valid addresses. Because of the space handling, the sender can add spaces to the beginning of the address and it will still be considered valid. In later steps this addresses are not longer valid.
Addresses starting with spaces are considered invalid in some locations of Postfix. What surprised me a bit is that virtual alias handling did not map them. The unmodified addressed showed up on the LMTP backend server. That's why they showed up my radar.
I would say Postfix is wrong in this case. The LDAP server applies the spec correctly and defines spaces in e-mail addresses as insignificant. Postfix on the other side considers them significant. The easiest fix would be to not allow any spaces in the LDAP table.