Long delays in mail delivery to mailboxes when msg is recieved at server

Mail arrives at Exchange server we know this because we have logging turned on, but the mail appears to go into limbo for anything up to 2 hours before it gets delivered to users mail box,  there is no difference between outlook client or if the
user logs on using owa, the email is not shown.  when exchange does decide which it does it will deliver all messages it has received in one go so all show up with in 30 seconds at the same time in users in box.  we have put on the recent Exchange
SP1 hopping this would solve the issue, the server is brand new and has 2tb of storage available  CPU is hardly doing anything.  all other aspects of server are normal file shares printing etc.  Just mail delivery is VERY VERY slow and then
it all comes at once.
We have tried restarting the server some times this does help other occasions it makes not difference.  server has I3-3420 cpu with 16gb ram.  This is driving us bonkers please can some body give us some guidance as what to do check or alter.
Thanks in advance.
Richard

Hi Richard,
I recommend you to do few testing to narrow-down the root cause 
Does this mail delivery getting delayed only for  external users or its both for internal and external users ?
How many Exchange servers  you have ? Is this a combination of HUB & CAS together if its 2013 or you have them Separately?
Do you have any antispam configured in your environment ?
Is there any antivirus installed in the exchange servers?
I would recommend you to run Get-TransportAgent and see the list of transport agents installed on your Exchange servers
As a part of testing i would suggest you to disable all the transport agents installed on the servers disable antivirus send a test email and check if the delay is happening or not . Also disable the exchange antispam if its installed and see if the mail
delay exists. Because mostly any transport agents acting in the categorization part might be causing this problem if their configuration has any problem.
Let us know the results so that we can proceed further.
Please mark as helpful if you find my contribution useful or as an answer if it does answer your question.That will encourage me - and others - to take time out to help you.
Regards, 
Sathish
Sathish

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    May 23 13:35:49 mail postfix/qmgr[2532]: 69A2D5E12F: from=<CNETNetworks#[email protected]>, size=18494, nrcpt=1 (queue active)
    May 23 13:35:49 mail postfix/smtpd[1240]: disconnect from unknown[142.27.144.50]
    May 23 13:48:21 mail postfix/smtpd[1299]: connect from unknown[142.27.144.50]
    May 23 13:48:21 mail postfix/smtpd[1299]: 2644A5E130: client=unknown[142.27.144.50]
    May 23 13:48:21 mail postfix/cleanup[1302]: 2644A5E130: message-id=<[email protected]>
    May 23 13:48:21 mail postfix/qmgr[2532]: 2644A5E130: from=<[email protected]>, size=2438, nrcpt=1 (queue active)
    May 23 13:48:21 mail postfix/smtpd[1299]: disconnect from unknown[142.27.144.50]
    May 23 13:50:30 mail postfix/smtpd[1315]: connect from unknown[142.27.144.50]
    May 23 13:50:30 mail postfix/smtpd[1315]: 91EE25E131: client=unknown[142.27.144.50]
    May 23 13:50:30 mail postfix/cleanup[1316]: 91EE25E131: message-id=<[email protected]>
    May 23 13:50:30 mail postfix/qmgr[2532]: 91EE25E131: from=<[email protected]>, size=1966, nrcpt=1 (queue active)
    May 23 13:50:30 mail postfix/smtpd[1315]: disconnect from unknown[142.27.144.50]
    May 23 13:57:09 mail postfix/smtpd[1343]: connect from unknown[142.27.144.50]
    May 23 13:57:09 mail postfix/smtpd[1343]: 60FF95E132: client=unknown[142.27.144.50]
    May 23 13:57:09 mail postfix/cleanup[1346]: 60FF95E132: message-id=<[email protected]@SMS>
    May 23 13:57:09 mail postfix/qmgr[2532]: 60FF95E132: from=<[email protected]>, size=1017, nrcpt=1 (queue active)
    May 23 13:57:09 mail postfix/smtpd[1343]: disconnect from unknown[142.27.144.50]
    The email access log has already scrolled farther than the emails in my list, so I won't include that unless asked.
    Thanks in advance for any help offered.
    Jeff
    Intel X-Serve, X-Serve RAID, all kinds of other goodies   Mac OS X (10.4.9)   Support about 2000 Macs

    A wealth of information on configuring/troubleshooting your email server can be found at:
    http://osx.topicdesk.com/
    I know your issues isn't particularly with SPAM, however I would try to following this tutorial on "Frontline SPAM Defense":
    http://osx.topicdesk.com/content/view/38/62/
    This fixed many of my email server issues. I would try this first.

  • Long delay getting new mail

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  • Long delay when sending non-btinternet mail

    We are using Outlook Express/Windows mail client, and there is a long long delay when sending mail.
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    It works without delays on other (non BT) home/business networks.
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  • Delayed mail delivery after Rollup 6 install

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    Disabling the cache mode means it's not using a OST instead it's online with exchange all the time, if the behavior is only seen when in cached mode then it's having difficulty synchronizing the OST, if you have users with large mailboxes this could be causing
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  • Long delay between send button and actual send in mail

    When sending messages in mail, there is a long delay between the time I hit the send button and the actual sending begins.  Message and attachment size have no bearing.  The delay is usually about 30 seconds, but sometimes longer.

    There was info in the detail window when I opened it.  Also, it was not immediately connecting to the server, but when I clicked back on the regular mail window to send a test message, the server connected instantly.  Below is all that was in the details window:
    CONNECTED Jan 19 11:45:53.387 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46ed49310 -- thread:0x1032788a0
    READ Jan 19 11:45:53.601 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46ed49310 -- thread:0x1032788a0
    * OK [CAPABILITY st11p00mm-iscream023 1M XAPPLEPUSHSERVICE IMAP4 IMAP4rev1 SASL-IR AUTH=ATOKEN AUTH=PLAIN] iSCREAM ready to rumble (1M:12460) st11p00mm-iscream023
    WROTE Jan 19 11:45:53.756 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46ed49310 -- thread:0x7fc46d52ec20
    1.39 AUTHENTICATE ATOKEN MTY2MDIwMDk3ADE2NjAyMDA5NwBBUUFBQUFCUSt2ZmVHNVNBMGNLbDBsRElwQkdkc0hXNk9mdnFNVWM 9
    READ Jan 19 11:45:53.844 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46ed49310 -- thread:0x7fc46d52ec20
    1.39 OK [CAPABILITY XAPPLEPUSHSERVICE IMAP4 IMAP4rev1 ACL QUOTA LITERAL+ NAMESPACE UIDPLUS CHILDREN BINARY UNSELECT SORT CATENATE URLAUTH LANGUAGE ESEARCH ESORT THREAD=ORDEREDSUBJECT THREAD=REFERENCES CONDSTORE ENABLE CONTEXT=SEARCH CONTEXT=SORT WITHIN SASL-IR SEARCHRES XSENDER X-NETSCAPE XSERVERINFO X-SUN-SORT ANNOTATE-EXPERIMENT-1 X-UNAUTHENTICATE X-SUN-IMAP X-ANNOTATEMORE XUM1 ID IDLE] User jfbohn1 logged in
    WROTE Jan 19 11:45:53.857 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46ed49310 -- thread:0x7fc46bd56e40
    2.39 ID ("name" "Mac OS X Mail" "version" "5.3 (1283)" "os" "Mac OS X" "os-version" "10.7.5 (11G63)" "vendor" "Apple Inc.")
    READ Jan 19 11:45:53.925 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46ed49310 -- thread:0x7fc46bd56e40
    * ID NIL
    2.39 OK Completed
    WROTE Jan 19 11:45:53.929 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46ed49310 -- thread:0x7fc46be61a30
    3.39 LIST "" ""
    READ Jan 19 11:45:53.996 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46ed49310 -- thread:0x7fc46be61a30
    * LIST (\Noselect) "/" ""
    3.39 OK Completed
    WROTE Jan 19 11:45:54.002 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46ed49310 -- thread:0x7fc46bd56e40
    4.39 LOGOUT
    CONNECTED Jan 19 12:33:43.623 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46d262650 -- thread:0x7fc46edb9cd0
    READ Jan 19 12:33:43.837 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46d262650 -- thread:0x7fc46edb9cd0
    * OK [CAPABILITY st11p00mm-iscream029 1M XAPPLEPUSHSERVICE IMAP4 IMAP4rev1 SASL-IR AUTH=ATOKEN AUTH=PLAIN] iSCREAM ready to rumble (1M:4364) st11p00mm-iscream029
    WROTE Jan 19 12:33:43.995 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46d262650 -- thread:0x7fc46ea98e90
    1.43 AUTHENTICATE ATOKEN MTY2MDIwMDk3ADE2NjAyMDA5NwBBUUFBQUFCUSt2ZmVHNVNBMGNLbDBsRElwQkdkc0hXNk9mdnFNVWM 9
    READ Jan 19 12:33:44.088 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46d262650 -- thread:0x7fc46ea98e90
    1.43 OK [CAPABILITY XAPPLEPUSHSERVICE IMAP4 IMAP4rev1 ACL QUOTA LITERAL+ NAMESPACE UIDPLUS CHILDREN BINARY UNSELECT SORT CATENATE URLAUTH LANGUAGE ESEARCH ESORT THREAD=ORDEREDSUBJECT THREAD=REFERENCES CONDSTORE ENABLE CONTEXT=SEARCH CONTEXT=SORT WITHIN SASL-IR SEARCHRES XSENDER X-NETSCAPE XSERVERINFO X-SUN-SORT ANNOTATE-EXPERIMENT-1 X-UNAUTHENTICATE X-SUN-IMAP X-ANNOTATEMORE XUM1 ID IDLE] User jfbohn1 logged in
    WROTE Jan 19 12:33:44.093 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46d262650 -- thread:0x7fc46d229320
    2.43 ID ("name" "Mac OS X Mail" "version" "5.3 (1283)" "os" "Mac OS X" "os-version" "10.7.5 (11G63)" "vendor" "Apple Inc.")
    READ Jan 19 12:33:44.162 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46d262650 -- thread:0x7fc46d229320
    * ID NIL
    2.43 OK Completed
    WROTE Jan 19 12:33:44.167 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46d262650 -- thread:0x7fc46d229320
    3.43 LIST "" ""
    READ Jan 19 12:33:44.235 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46d262650 -- thread:0x7fc46d229320
    * LIST (\Noselect) "/" ""
    3.43 OK Completed
    WROTE Jan 19 12:33:44.241 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46d262650 -- thread:0x7fc46ea98e90
    4.43 LOGOUT
    CONNECTED Jan 19 12:34:12.742 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46edb7cf0 -- thread:0x7fc46d2e4d20
    READ Jan 19 12:34:12.957 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46edb7cf0 -- thread:0x7fc46d2e4d20
    * OK [CAPABILITY st11p00mm-iscream020 1M XAPPLEPUSHSERVICE IMAP4 IMAP4rev1 SASL-IR AUTH=ATOKEN AUTH=PLAIN] iSCREAM ready to rumble (1M:32403) st11p00mm-iscream020
    WROTE Jan 19 12:34:13.116 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46edb7cf0 -- thread:0x7fc46edc5c40
    1.44 AUTHENTICATE ATOKEN MTY2MDIwMDk3ADE2NjAyMDA5NwBBUUFBQUFCUSt2ZmVHNVNBMGNLbDBsRElwQkdkc0hXNk9mdnFNVWM 9
    READ Jan 19 12:34:13.204 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46edb7cf0 -- thread:0x7fc46edc5c40
    1.44 OK [CAPABILITY XAPPLEPUSHSERVICE IMAP4 IMAP4rev1 ACL QUOTA LITERAL+ NAMESPACE UIDPLUS CHILDREN BINARY UNSELECT SORT CATENATE URLAUTH LANGUAGE ESEARCH ESORT THREAD=ORDEREDSUBJECT THREAD=REFERENCES CONDSTORE ENABLE CONTEXT=SEARCH CONTEXT=SORT WITHIN SASL-IR SEARCHRES XSENDER X-NETSCAPE XSERVERINFO X-SUN-SORT ANNOTATE-EXPERIMENT-1 X-UNAUTHENTICATE X-SUN-IMAP X-ANNOTATEMORE XUM1 ID IDLE] User jfbohn1 logged in
    WROTE Jan 19 12:34:13.211 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46edb7cf0 -- thread:0x7fc46d56a3d0
    2.44 ID ("name" "Mac OS X Mail" "version" "5.3 (1283)" "os" "Mac OS X" "os-version" "10.7.5 (11G63)" "vendor" "Apple Inc.")
    READ Jan 19 12:34:13.280 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46edb7cf0 -- thread:0x7fc46d56a3d0
    * ID NIL
    2.44 OK Completed
    WROTE Jan 19 12:34:13.287 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46edb7cf0 -- thread:0x7fc46ed7ba30
    3.44 LIST "" ""
    READ Jan 19 12:34:13.355 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46edb7cf0 -- thread:0x7fc46ed7ba30
    * LIST (\Noselect) "/" ""
    3.44 OK Completed
    WROTE Jan 19 12:34:13.363 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:p02-imap.mail.me.com -- port:993 -- socket:0x7fc46edb7cf0 -- thread:0x7fc46d56a3d0
    4.44 LOGOUT
    CONNECTED Jan 19 12:34:58.696 [kCFStreamSocketSecurityLevelNone]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    READ Jan 19 12:34:58.763 [kCFStreamSocketSecurityLevelNone]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    220 st11p02mm-asmtp003.mac.com -- Server ESMTP (Oracle Communications Messaging Server 7u4-24.01(7.0.4.24.0) 64bit (built Jan  3 2012))
    WROTE Jan 19 12:35:28.779 [kCFStreamSocketSecurityLevelNone]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    EHLO [192.168.1.30]
    READ Jan 19 12:35:28.846 [kCFStreamSocketSecurityLevelNone]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    250-st11p02mm-asmtp003.mac.com
    250-8BITMIME
    250-PIPELINING
    250-CHUNKING
    250-DSN
    250-ENHANCEDSTATUSCODES
    250-EXPN
    250-HELP
    250-XADR
    250-XSTA
    250-XCIR
    250-XGEN
    250-XLOOP 9DDFE32F5FFD44C1C6F842687D47D955
    250-STARTTLS
    250-NO-SOLICITING
    250 SIZE 0
    WROTE Jan 19 12:35:28.851 [kCFStreamSocketSecurityLevelNone]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    STARTTLS
    READ Jan 19 12:35:28.917 [kCFStreamSocketSecurityLevelNone]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    220 2.5.0 Go ahead with TLS negotiation.
    WROTE Jan 19 12:35:29.288 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    EHLO [192.168.1.30]
    READ Jan 19 12:35:29.355 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    250-st11p02mm-asmtp003.mac.com
    250-8BITMIME
    250-PIPELINING
    250-CHUNKING
    250-DSN
    250-ENHANCEDSTATUSCODES
    250-EXPN
    250-HELP
    250-XADR
    250-XSTA
    250-XCIR
    250-XGEN
    250-XLOOP 9DDFE32F5FFD44C1C6F842687D47D955
    250-AUTH PLAIN LOGIN ATOKEN WSTOKEN WETOKEN
    250-AUTH=LOGIN PLAIN
    250-NO-SOLICITING
    250 SIZE 0
    WROTE Jan 19 12:35:29.363 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    EHLO [192.168.1.30]
    READ Jan 19 12:35:29.429 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    250-st11p02mm-asmtp003.mac.com
    250-8BITMIME
    250-PIPELINING
    250-CHUNKING
    250-DSN
    250-ENHANCEDSTATUSCODES
    250-EXPN
    250-HELP
    250-XADR
    250-XSTA
    250-XCIR
    250-XGEN
    250-XLOOP 9DDFE32F5FFD44C1C6F842687D47D955
    250-AUTH PLAIN LOGIN ATOKEN WSTOKEN WETOKEN
    250-AUTH=LOGIN PLAIN
    250-NO-SOLICITING
    250 SIZE 0
    WROTE Jan 19 12:35:29.539 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    AUTH ATOKEN MTY2MDIwMDk3ADE2NjAyMDA5NwBBUUFBQUFCUSt2ZmVHNVNBMGNLbDBsRElwQkdkc0hXNk9mdnFNVWM 9
    READ Jan 19 12:35:29.618 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    235 2.7.0 ATOKEN authentication successful.
    WROTE Jan 19 12:35:29.628 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    MAIL FROM:<****>
    READ Jan 19 12:35:29.700 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    250 2.5.0 Address Ok.
    WROTE Jan 19 12:35:29.708 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    RCPT TO:<****>
    READ Jan 19 12:35:29.912 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    250 2.1.5 **** OK.
    WROTE Jan 19 12:35:29.921 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    DATA
    READ Jan 19 12:35:29.986 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    354 Enter mail, end with a single ".".
    WROTE Jan 19 12:35:29.995 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    From: John Bohn <****>
    Content-Type: text/plain; charset=us-ascii
    Content-Transfer-Encoding: 7bit
    Subject: test server
    Date: Sat, 19 Jan 2013 12:34:58 -0800
    Message-Id: <****>
    To: John Bohn <****>
    Mime-Version: 1.0 (Apple Message framework v1283)
    X-Mailer: Apple Mail (2.1283)
    asdfs
    READ Jan 19 12:35:30.197 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:p02-smtp.mail.me.com -- port:587 -- socket:0x7fc46d2c7f80 -- thread:0x7fc470567950
    250 2.5.0 Ok, envelope id ****
    <Email Edited By Host>

  • When I get an alert from my car sat nav the music on my iphone has a long delay before it comes back on and misses a part of the track why does it do this.

    When I get an alert from my car sat nav the music on my iphone has a long delay before it comes back on and misses a part of the track why does it do this.
    It only seems to do this since an iphone download last year.......its driving me mad !

    See:
    Recovering your iTunes library from your iPod or iOS device: Apple Support Communities
    To copy iTunes purchases to the computer you have to log into (authorize) the account that purchased them and them transfer
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