Why does iOS 5 fail to connect to a server running JDK 1.6, but not JDK 1.5

Question

We have a Java Socket Server listening on an SSLSocket (port 443) and an iOS application that connects with it. When running on iOS 5.1, the application stopped working when we upgraded the Java version of the server from JDK 1.5 to 1.6 (or 1.7). The app connects just fine to JDK 5 and 6 when running on iOS 6.

The iOS app is reporting an error: -9809 = errSSLCrypto. On the Java side, we get javax.net.ssl.SSLException: Received fatal alert: close_notify.

On the Java server side, we have enabled all the available cipher suites. On the client side we have tested enabling several different suites, although we have yet to complete a test involving each one individually enabled. Right now, it is failing when we use TLS_DH_anon_WITH_AES_128_CBC_SHA although it has failed with others and we are starting to think it's not the suite.

Here is the debug output. It makes it all the way to ServerHelloDone and then fails shortly thereafter:

Is secure renegotiation: false
[Raw read]: length = 5
0000: 16 03 03 00 41                                     ....A
[Raw read]: length = 65
0000: 01 00 00 3D 03 03 50 83   1E 0B 56 19 25 65 C8 F2  ...=..P...V.%e..
0010: AF 02 AD 48 FE E2 92 CF   B8 D7 A6 A3 EA C5 FF 5D  ...H...........]
0020: 74 0F 1B C1 99 18 00 00   08 00 FF 00 34 00 1B 00  t...........4...
0030: 18 01 00 00 0C 00 0D 00   08 00 06 05 01 04 01 02  ................
0040: 01                                                 .
URT-, READ: Unknown-3.3 Handshake, length = 65
*** ClientHello, Unknown-3.3
RandomCookie:  GMT: 1333992971 bytes = { 86, 25, 37, 101, 200, 242, 175, 2, 173, 72, 254, 226, 146, 207, 184, 215, 166, 163, 234, 197, 255, 93, 116, 15, 27, 193, 153, 24 }
Session ID:  {}
Cipher Suites: [TLS_EMPTY_RENEGOTIATION_INFO_SCSV, TLS_DH_anon_WITH_AES_128_CBC_SHA, SSL_DH_anon_WITH_3DES_EDE_CBC_SHA, SSL_DH_anon_WITH_RC4_128_MD5]
Compression Methods:  { 0 }
Unsupported extension signature_algorithms, data: 00:06:05:01:04:01:02:01
***
[read] MD5 and SHA1 hashes:  len = 65
0000: 01 00 00 3D 03 03 50 83   1E 0B 56 19 25 65 C8 F2  ...=..P...V.%e..
0010: AF 02 AD 48 FE E2 92 CF   B8 D7 A6 A3 EA C5 FF 5D  ...H...........]
0020: 74 0F 1B C1 99 18 00 00   08 00 FF 00 34 00 1B 00  t...........4...
0030: 18 01 00 00 0C 00 0D 00   08 00 06 05 01 04 01 02  ................
0040: 01                                                 .
%% Created:  [Session-1, TLS_DH_anon_WITH_AES_128_CBC_SHA]
*** ServerHello, TLSv1
RandomCookie:  GMT: 1333992972 bytes = { 100, 3, 56, 153, 7, 2, 251, 64, 41, 32, 66, 240, 227, 181, 55, 190, 2, 237, 146, 0, 73, 119, 70, 0, 160, 9, 28, 207 }
Session ID:  {80, 131, 30, 12, 241, 73, 52, 38, 46, 41, 237, 226, 199, 246, 156, 45, 3, 247, 182, 43, 223, 8, 49, 169, 188, 63, 160, 41, 102, 199, 50, 190}
Cipher Suite: TLS_DH_anon_WITH_AES_128_CBC_SHA
Compression Method: 0
Extension renegotiation_info, renegotiated_connection: <empty>
***
Cipher suite:  TLS_DH_anon_WITH_AES_128_CBC_SHA
*** Diffie-Hellman ServerKeyExchange
DH Modulus:  { 233, 230, 66, 89, 157, 53, 95, 55, 201, 127, 253, 53, 103, 18, 11, 142, 37, 201, 205, 67, 233, 39, 179, 169, 103, 15, 190, 197, 216, 144, 20, 25, 34, 210, 195, 179, 173, 36, 128, 9, 55, 153, 134, 157, 30, 132, 106, 171, 73, 250, 176, 173, 38, 210, 206, 106, 34, 33, 157, 71, 11, 206, 125, 119, 125, 74, 33, 251, 233, 194, 112, 181, 127, 96, 112, 2, 243, 206, 248, 57, 54, 148, 207, 69, 238, 54, 136, 193, 26, 140, 86, 171, 18, 122, 61, 175 }
DH Base:  { 48, 71, 10, 213, 160, 5, 251, 20, 206, 45, 157, 205, 135, 227, 139, 199, 209, 177, 197, 250, 203, 174, 203, 233, 95, 25, 10, 167, 163, 29, 35, 196, 219, 188, 190, 6, 23, 69, 68, 64, 26, 91, 44, 2, 9, 101, 216, 194, 189, 33, 113, 211, 102, 132, 69, 119, 31, 116, 186, 8, 77, 32, 41, 216, 60, 28, 21, 133, 71, 243, 169, 241, 162, 113, 91, 226, 61, 81, 174, 77, 62, 90, 31, 106, 112, 100, 243, 22, 147, 58, 52, 109, 63, 82, 146, 82 }
Server DH Public Key:  { 8, 60, 59, 13, 224, 110, 32, 168, 116, 139, 246, 146, 15, 12, 216, 107, 82, 182, 140, 80, 193, 237, 159, 189, 87, 34, 18, 197, 181, 252, 26, 27, 94, 160, 188, 162, 30, 29, 165, 165, 68, 152, 11, 204, 251, 187, 14, 233, 239, 103, 134, 168, 181, 173, 206, 151, 197, 128, 65, 239, 233, 191, 29, 196, 93, 80, 217, 55, 81, 240, 101, 31, 119, 98, 188, 211, 52, 146, 168, 127, 127, 66, 63, 111, 198, 134, 70, 213, 31, 162, 146, 25, 178, 79, 56, 116 }
Anonymous
*** ServerHelloDone
[write] MD5 and SHA1 hashes:  len = 383
0000: 02 00 00 4D 03 01 50 83   1E 0C 64 03 38 99 07 02  ...M..P...d.8...
0010: FB 40 29 20 42 F0 E3 B5   37 BE 02 ED 92 00 49 77  .@) B...7.....Iw
0020: 46 00 A0 09 1C CF 20 50   83 1E 0C F1 49 34 26 2E  F..... P....I4&.
0030: 29 ED E2 C7 F6 9C 2D 03   F7 B6 2B DF 08 31 A9 BC  ).....-...+..1..
0040: 3F A0 29 66 C7 32 BE 00   34 00 00 05 FF 01 00 01  ?.)f.2..4.......
0050: 00 0C 00 01 26 00 60 E9   E6 42 59 9D 35 5F 37 C9  ....&.`..BY.5_7.
0060: 7F FD 35 67 12 0B 8E 25   C9 CD 43 E9 27 B3 A9 67  ..5g...%..C.'..g
0070: 0F BE C5 D8 90 14 19 22   D2 C3 B3 AD 24 80 09 37  ......."....$..7
0080: 99 86 9D 1E 84 6A AB 49   FA B0 AD 26 D2 CE 6A 22  .....j.I...&..j"
0090: 21 9D 47 0B CE 7D 77 7D   4A 21 FB E9 C2 70 B5 7F  !.G...w.J!...p..
00A0: 60 70 02 F3 CE F8 39 36   94 CF 45 EE 36 88 C1 1A  `p....96..E.6...
00B0: 8C 56 AB 12 7A 3D AF 00   60 30 47 0A D5 A0 05 FB  .V..z=..`0G.....
00C0: 14 CE 2D 9D CD 87 E3 8B   C7 D1 B1 C5 FA CB AE CB  ..-.............
00D0: E9 5F 19 0A A7 A3 1D 23   C4 DB BC BE 06 17 45 44  ._.....#......ED
00E0: 40 1A 5B 2C 02 09 65 D8   C2 BD 21 71 D3 66 84 45  @.[,..e...!q.f.E
00F0: 77 1F 74 BA 08 4D 20 29   D8 3C 1C 15 85 47 F3 A9  w.t..M ).<...G..
0100: F1 A2 71 5B E2 3D 51 AE   4D 3E 5A 1F 6A 70 64 F3  ..q[.=Q.M>Z.jpd.
0110: 16 93 3A 34 6D 3F 52 92   52 00 60 08 3C 3B 0D E0  ..:4m?R.R.`.<;..
0120: 6E 20 A8 74 8B F6 92 0F   0C D8 6B 52 B6 8C 50 C1  n .t......kR..P.
0130: ED 9F BD 57 22 12 C5 B5   FC 1A 1B 5E A0 BC A2 1E  ...W"......^....
0140: 1D A5 A5 44 98 0B CC FB   BB 0E E9 EF 67 86 A8 B5  ...D........g...
0150: AD CE 97 C5 80 41 EF E9   BF 1D C4 5D 50 D9 37 51  .....A.....]P.7Q
0160: F0 65 1F 77 62 BC D3 34   92 A8 7F 7F 42 3F 6F C6  .e.wb..4....B?o.
0170: 86 46 D5 1F A2 92 19 B2   4F 38 74 0E 00 00 00     .F......O8t....
URT-, WRITE: TLSv1 Handshake, length = 383
[Raw write]: length = 388
0000: 16 03 01 01 7F 02 00 00   4D 03 01 50 83 1E 0C 64  ........M..P...d
0010: 03 38 99 07 02 FB 40 29   20 42 F0 E3 B5 37 BE 02  .8....@) B...7..
0020: ED 92 00 49 77 46 00 A0   09 1C CF 20 50 83 1E 0C  ...IwF..... P...
0030: F1 49 34 26 2E 29 ED E2   C7 F6 9C 2D 03 F7 B6 2B  .I4&.).....-...+
0040: DF 08 31 A9 BC 3F A0 29   66 C7 32 BE 00 34 00 00  ..1..?.)f.2..4..
0050: 05 FF 01 00 01 00 0C 00   01 26 00 60 E9 E6 42 59  .........&.`..BY
0060: 9D 35 5F 37 C9 7F FD 35   67 12 0B 8E 25 C9 CD 43  .5_7...5g...%..C
0070: E9 27 B3 A9 67 0F BE C5   D8 90 14 19 22 D2 C3 B3  .'..g......."...
0080: AD 24 80 09 37 99 86 9D   1E 84 6A AB 49 FA B0 AD  .$..7.....j.I...
0090: 26 D2 CE 6A 22 21 9D 47   0B CE 7D 77 7D 4A 21 FB  &..j"!.G...w.J!.
00A0: E9 C2 70 B5 7F 60 70 02   F3 CE F8 39 36 94 CF 45  ..p..`p....96..E
00B0: EE 36 88 C1 1A 8C 56 AB   12 7A 3D AF 00 60 30 47  .6....V..z=..`0G
00C0: 0A D5 A0 05 FB 14 CE 2D   9D CD 87 E3 8B C7 D1 B1  .......-........
00D0: C5 FA CB AE CB E9 5F 19   0A A7 A3 1D 23 C4 DB BC  ......_.....#...
00E0: BE 06 17 45 44 40 1A 5B   2C 02 09 65 D8 C2 BD 21  ...ED@.[,..e...!
00F0: 71 D3 66 84 45 77 1F 74   BA 08 4D 20 29 D8 3C 1C  q.f.Ew.t..M ).<.
0100: 15 85 47 F3 A9 F1 A2 71   5B E2 3D 51 AE 4D 3E 5A  ..G....q[.=Q.M>Z
0110: 1F 6A 70 64 F3 16 93 3A   34 6D 3F 52 92 52 00 60  .jpd...:4m?R.R.`
0120: 08 3C 3B 0D E0 6E 20 A8   74 8B F6 92 0F 0C D8 6B  .<;..n .t......k
0130: 52 B6 8C 50 C1 ED 9F BD   57 22 12 C5 B5 FC 1A 1B  R..P....W"......
0140: 5E A0 BC A2 1E 1D A5 A5   44 98 0B CC FB BB 0E E9  ^.......D.......
0150: EF 67 86 A8 B5 AD CE 97   C5 80 41 EF E9 BF 1D C4  .g........A.....
0160: 5D 50 D9 37 51 F0 65 1F   77 62 BC D3 34 92 A8 7F  ]P.7Q.e.wb..4...
0170: 7F 42 3F 6F C6 86 46 D5   1F A2 92 19 B2 4F 38 74  .B?o..F......O8t
0180: 0E 00 00 00                                        ....
[Raw read]: length = 5
0000: 15 03 01 00 02                                     .....
[Raw read]: length = 2
0000: 02 00                                              ..
URT-, READ: TLSv1 Alert, length = 2
URT-, RECV TLSv1 ALERT:  fatal, close_notify
URT-, called closeSocket()
URT-, handling exception: javax.net.ssl.SSLException: Received fatal alert: close_notify

FYI, this works in iOS 6.0

Answer 1

Have you tried exporting a "new" self signed certificate from the Java server and import to the trust store of your app/OS?