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🐛 Fix #inspect output when SSLSocket#connect fails #764

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Merged
nevans merged 2 commits into from
Sep 9, 2026
Merged

🐛 Fix #inspect output when SSLSocket#connect fails #764

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a945a9d
✅ Improve TLS/STARTTLS tests
nevans Sep 9, 2026
6fe0796
🐛 Fix #inspect when TLS connect fails
nevans Sep 9, 2026
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5 changes: 3 additions & 2 deletions lib/net/imap.rb
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Original file line number Diff line number Diff line change
Expand Up @@ -1240,7 +1240,7 @@ def initialize(host, port: nil, ssl: nil, response_handlers: nil,
@greeting = nil
@capabilities = nil
@enabled = Set.new
@tls_verified = false
@tls_connected = @tls_verified = false
@connection_state = ConnectionState::NotAuthenticated.new

# Client Protocol Receiver
Expand Down Expand Up @@ -1302,7 +1302,7 @@ def inspect
if tls_verified?
"TLS"
elsif ssl_ctx && @sock.kind_of?(OpenSSL::SSL::SSLSocket)
"TLS (#{@sock.session ? "NOT VERIFIED" : "NOT ESTABLISHED"})"
"TLS (#{@tls_connected ? "NOT VERIFIED" : "NOT ESTABLISHED"})"
else
"PLAINTEXT#{" (TLS NOT STARTED)" if ssl_ctx}"
end
Expand Down Expand Up @@ -4129,6 +4129,7 @@ def start_tls_session
@sock.sync_close = true
@sock.hostname = @host if @sock.respond_to? :hostname=
ssl_socket_connect(@sock, open_timeout)
@tls_connected = true
if ssl_ctx.verify_mode != OpenSSL::SSL::VERIFY_NONE
@sock.post_connection_check(@host)
@tls_verified = true
Expand Down
39 changes: 30 additions & 9 deletions test/net/imap/test_imap_tls.rb
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Original file line number Diff line number Diff line change
Expand Up @@ -30,6 +30,30 @@ def test_imaps_unknown_ca
end
end

def assert_tls_unstarted(imap) = assert_tls_stage imap, :unstarted
def assert_tls_incomplete(imap) = assert_tls_stage imap, :incomplete
def assert_tls_unverified(imap) = assert_tls_stage imap, :unverified
def assert_tls_verified(imap) = assert_tls_stage imap, :verified

INSPECT_INCLUDES = {
unstarted: " PLAINTEXT (TLS NOT STARTED) disconnected",
incomplete: " TLS (NOT ESTABLISHED) disconnected",
unverified: " TLS (NOT VERIFIED) disconnected",
verified: " TLS disconnected",
}

def assert_tls_stage(imap, stage)
verified = stage == :verified
assert imap.ssl_ctx_params.frozen?, "#ssl_ctx_params should be frozen"
assert_kind_of Hash, imap.ssl_ctx_params,
"#ssl_ctx_params should be a Hash"
assert_kind_of OpenSSL::SSL::SSLContext, imap.ssl_ctx,
"#ssl_ctx should be an OpenSSL::SSL::SSLContext"
assert_equal verified, imap.tls_verified?,
"#tls_verified? should be #{verified}"
assert_include imap.inspect, INSPECT_INCLUDES.fetch(stage)
end

def test_imaps_with_ca_file
# Assert verified *after* the imaps_test and assert_nothing_raised blocks.
# Otherwise, failures can't logout and need to wait for the timeout.
Expand All @@ -50,7 +74,7 @@ def test_imaps_with_ca_file
end
end
assert_equal true, verified
assert_equal true, imap.tls_verified?
assert_tls_verified imap
assert_equal({ca_file: CA_FILE}, imap.ssl_ctx_params)
assert_equal(CA_FILE, imap.ssl_ctx.ca_file)
assert_equal(OpenSSL::SSL::VERIFY_PEER, imap.ssl_ctx.verify_mode)
Expand All @@ -77,7 +101,7 @@ def test_imaps_verify_none
end
end
assert_equal false, verified
assert_equal false, imap.tls_verified?
assert_tls_unverified imap
assert_equal({verify_mode: OpenSSL::SSL::VERIFY_NONE},
imap.ssl_ctx_params)
assert_equal(nil, imap.ssl_ctx.ca_file)
Expand Down Expand Up @@ -111,7 +135,7 @@ def test_starttls_unknown_ca
end
assert_kind_of(OpenSSL::SSL::SSLError, ex)
assert_local_backtrace ex
assert_equal false, imap.tls_verified?
assert_tls_incomplete imap
assert_equal({}, imap.ssl_ctx_params)
assert_equal(nil, imap.ssl_ctx.ca_file)
assert_equal(OpenSSL::SSL::VERIFY_PEER, imap.ssl_ctx.verify_mode)
Expand All @@ -131,8 +155,7 @@ def test_starttls
assert_equal false, initial_verified
assert_equal false, initial_params
assert_equal nil, initial_ctx
assert_equal true, imap.tls_verified?
assert_include imap.inspect, " TLS disconnected"
assert_tls_verified imap
assert_equal({ca_file: CA_FILE}, imap.ssl_ctx_params)
rescue SystemCallError
skip $!
Expand Down Expand Up @@ -167,8 +190,7 @@ def test_starttls_stripping_not_ok
imap.disconnect if imap && !imap.disconnected?
end

assert_equal false, imap.tls_verified?
assert_include imap.inspect, " PLAINTEXT (TLS NOT STARTED) "
assert_tls_unstarted imap
assert_equal({ca_file: CA_FILE}, imap.ssl_ctx_params)
assert_equal(CA_FILE, imap.ssl_ctx.ca_file)
assert_equal(OpenSSL::SSL::VERIFY_PEER, imap.ssl_ctx.verify_mode)
Expand Down Expand Up @@ -214,8 +236,7 @@ def test_starttls_stripping_ok_sent_before_response
ensure
imap.disconnect if imap && !imap.disconnected?
end
assert_equal false, imap.tls_verified?
assert_include imap.inspect, " PLAINTEXT (TLS NOT STARTED) "
assert_tls_unstarted imap
assert_equal({ca_file: CA_FILE}, imap.ssl_ctx_params)
assert_equal(CA_FILE, imap.ssl_ctx.ca_file)
assert_equal(OpenSSL::SSL::VERIFY_PEER, imap.ssl_ctx.verify_mode)
Expand Down
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