Can't send mail with Apple Mail with Outlook.com due to SMTP











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To preface, I know for a fact that the password I am using is correct as per outlook.com's instructions and every tutorial I can get my hands on. It should be my password I use to enter the account, and IMAP is working beautifully. If it matters, I'm running Mavericks.



I get the following issue when I connect my outlook.com/live.com account with the Apple Mail app:



An error occurred while sending this message using the SMTP server “(null)”


It's the most vague error message I could get, next to:



"Trying to log in to this SMTP account failed. Verify that the username and password are correct."


The logs show this though:



WROTE Aug 30 14:45:10.421 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x6080008c9ca0 -- thread:0x608001467540
AUTH PLAIN (*** 64 bytes hidden ***)


My theory was a TLS issue, but it seems that it is using it according to the logs despite my inability to select it in the app.










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    up vote
    0
    down vote

    favorite












    To preface, I know for a fact that the password I am using is correct as per outlook.com's instructions and every tutorial I can get my hands on. It should be my password I use to enter the account, and IMAP is working beautifully. If it matters, I'm running Mavericks.



    I get the following issue when I connect my outlook.com/live.com account with the Apple Mail app:



    An error occurred while sending this message using the SMTP server “(null)”


    It's the most vague error message I could get, next to:



    "Trying to log in to this SMTP account failed. Verify that the username and password are correct."


    The logs show this though:



    WROTE Aug 30 14:45:10.421 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x6080008c9ca0 -- thread:0x608001467540
    AUTH PLAIN (*** 64 bytes hidden ***)


    My theory was a TLS issue, but it seems that it is using it according to the logs despite my inability to select it in the app.










    share|improve this question
























      up vote
      0
      down vote

      favorite









      up vote
      0
      down vote

      favorite











      To preface, I know for a fact that the password I am using is correct as per outlook.com's instructions and every tutorial I can get my hands on. It should be my password I use to enter the account, and IMAP is working beautifully. If it matters, I'm running Mavericks.



      I get the following issue when I connect my outlook.com/live.com account with the Apple Mail app:



      An error occurred while sending this message using the SMTP server “(null)”


      It's the most vague error message I could get, next to:



      "Trying to log in to this SMTP account failed. Verify that the username and password are correct."


      The logs show this though:



      WROTE Aug 30 14:45:10.421 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x6080008c9ca0 -- thread:0x608001467540
      AUTH PLAIN (*** 64 bytes hidden ***)


      My theory was a TLS issue, but it seems that it is using it according to the logs despite my inability to select it in the app.










      share|improve this question













      To preface, I know for a fact that the password I am using is correct as per outlook.com's instructions and every tutorial I can get my hands on. It should be my password I use to enter the account, and IMAP is working beautifully. If it matters, I'm running Mavericks.



      I get the following issue when I connect my outlook.com/live.com account with the Apple Mail app:



      An error occurred while sending this message using the SMTP server “(null)”


      It's the most vague error message I could get, next to:



      "Trying to log in to this SMTP account failed. Verify that the username and password are correct."


      The logs show this though:



      WROTE Aug 30 14:45:10.421 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x6080008c9ca0 -- thread:0x608001467540
      AUTH PLAIN (*** 64 bytes hidden ***)


      My theory was a TLS issue, but it seems that it is using it according to the logs despite my inability to select it in the app.







      macos email smtp apple-mail outlook.com






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      share|improve this question











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      share|improve this question










      asked Aug 30 '14 at 22:02









      doge

      112




      112






















          2 Answers
          2






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          up vote
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          These are the settings I use to achieve the same thing...



          smtp.outlook.com, with SSL

          port: 587
          authentication: Password

          user name: full email address

          TLS cert: None



          If by any chance, that's on a BT-hosted office 365 account, the host names are changing soon, to outlook.office365.com for pop3 & smtp.office365.com for smtp; the other data remains the same. I've seen some outages over the past month on the old URLs. I switched mine to the new ones recently & have had no issues since, but officially, the change-over won't be until next year.

          [All irrelevant, of course, if you're not on BT]



          Setup pics included showing new office 365 settings, for the older outlook.com, just change that section, rest is the same.



          setup screen 1



          setup screen 2



          setup screen 3






          share|improve this answer























          • Is that a comment, or a suggested set of settings?
            – Journeyman Geek
            Aug 31 '14 at 9:55










          • it's the settings I use on my machine to achieve the same thing. I'll fix up the reply a bit - was 1st coffee when I wrote it
            – Tetsujin
            Aug 31 '14 at 9:58






          • 1




            Awesome. Formatting wise, a sanitised screenshot of the settings page would probably be clearer too
            – Journeyman Geek
            Aug 31 '14 at 11:24










          • Added. Hope it's still useful with that much info blurred out.
            – Tetsujin
            Aug 31 '14 at 11:48


















          up vote
          0
          down vote













          It is a bug in Mail; go to Mail, then preferences, then select the account you are having problems with; highlight the outgoing server that does NOT say "offline" then save this setting and try again; worked for me.






          share|improve this answer





















          • Can you clarify what setting to save? It sounds like your instructions don't change anything.
            – fixer1234
            Jan 30 '15 at 5:50











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          2 Answers
          2






          active

          oldest

          votes








          2 Answers
          2






          active

          oldest

          votes









          active

          oldest

          votes






          active

          oldest

          votes








          up vote
          0
          down vote













          These are the settings I use to achieve the same thing...



          smtp.outlook.com, with SSL

          port: 587
          authentication: Password

          user name: full email address

          TLS cert: None



          If by any chance, that's on a BT-hosted office 365 account, the host names are changing soon, to outlook.office365.com for pop3 & smtp.office365.com for smtp; the other data remains the same. I've seen some outages over the past month on the old URLs. I switched mine to the new ones recently & have had no issues since, but officially, the change-over won't be until next year.

          [All irrelevant, of course, if you're not on BT]



          Setup pics included showing new office 365 settings, for the older outlook.com, just change that section, rest is the same.



          setup screen 1



          setup screen 2



          setup screen 3






          share|improve this answer























          • Is that a comment, or a suggested set of settings?
            – Journeyman Geek
            Aug 31 '14 at 9:55










          • it's the settings I use on my machine to achieve the same thing. I'll fix up the reply a bit - was 1st coffee when I wrote it
            – Tetsujin
            Aug 31 '14 at 9:58






          • 1




            Awesome. Formatting wise, a sanitised screenshot of the settings page would probably be clearer too
            – Journeyman Geek
            Aug 31 '14 at 11:24










          • Added. Hope it's still useful with that much info blurred out.
            – Tetsujin
            Aug 31 '14 at 11:48















          up vote
          0
          down vote













          These are the settings I use to achieve the same thing...



          smtp.outlook.com, with SSL

          port: 587
          authentication: Password

          user name: full email address

          TLS cert: None



          If by any chance, that's on a BT-hosted office 365 account, the host names are changing soon, to outlook.office365.com for pop3 & smtp.office365.com for smtp; the other data remains the same. I've seen some outages over the past month on the old URLs. I switched mine to the new ones recently & have had no issues since, but officially, the change-over won't be until next year.

          [All irrelevant, of course, if you're not on BT]



          Setup pics included showing new office 365 settings, for the older outlook.com, just change that section, rest is the same.



          setup screen 1



          setup screen 2



          setup screen 3






          share|improve this answer























          • Is that a comment, or a suggested set of settings?
            – Journeyman Geek
            Aug 31 '14 at 9:55










          • it's the settings I use on my machine to achieve the same thing. I'll fix up the reply a bit - was 1st coffee when I wrote it
            – Tetsujin
            Aug 31 '14 at 9:58






          • 1




            Awesome. Formatting wise, a sanitised screenshot of the settings page would probably be clearer too
            – Journeyman Geek
            Aug 31 '14 at 11:24










          • Added. Hope it's still useful with that much info blurred out.
            – Tetsujin
            Aug 31 '14 at 11:48













          up vote
          0
          down vote










          up vote
          0
          down vote









          These are the settings I use to achieve the same thing...



          smtp.outlook.com, with SSL

          port: 587
          authentication: Password

          user name: full email address

          TLS cert: None



          If by any chance, that's on a BT-hosted office 365 account, the host names are changing soon, to outlook.office365.com for pop3 & smtp.office365.com for smtp; the other data remains the same. I've seen some outages over the past month on the old URLs. I switched mine to the new ones recently & have had no issues since, but officially, the change-over won't be until next year.

          [All irrelevant, of course, if you're not on BT]



          Setup pics included showing new office 365 settings, for the older outlook.com, just change that section, rest is the same.



          setup screen 1



          setup screen 2



          setup screen 3






          share|improve this answer














          These are the settings I use to achieve the same thing...



          smtp.outlook.com, with SSL

          port: 587
          authentication: Password

          user name: full email address

          TLS cert: None



          If by any chance, that's on a BT-hosted office 365 account, the host names are changing soon, to outlook.office365.com for pop3 & smtp.office365.com for smtp; the other data remains the same. I've seen some outages over the past month on the old URLs. I switched mine to the new ones recently & have had no issues since, but officially, the change-over won't be until next year.

          [All irrelevant, of course, if you're not on BT]



          Setup pics included showing new office 365 settings, for the older outlook.com, just change that section, rest is the same.



          setup screen 1



          setup screen 2



          setup screen 3







          share|improve this answer














          share|improve this answer



          share|improve this answer








          edited Aug 31 '14 at 11:47

























          answered Aug 31 '14 at 7:48









          Tetsujin

          15.2k53260




          15.2k53260












          • Is that a comment, or a suggested set of settings?
            – Journeyman Geek
            Aug 31 '14 at 9:55










          • it's the settings I use on my machine to achieve the same thing. I'll fix up the reply a bit - was 1st coffee when I wrote it
            – Tetsujin
            Aug 31 '14 at 9:58






          • 1




            Awesome. Formatting wise, a sanitised screenshot of the settings page would probably be clearer too
            – Journeyman Geek
            Aug 31 '14 at 11:24










          • Added. Hope it's still useful with that much info blurred out.
            – Tetsujin
            Aug 31 '14 at 11:48


















          • Is that a comment, or a suggested set of settings?
            – Journeyman Geek
            Aug 31 '14 at 9:55










          • it's the settings I use on my machine to achieve the same thing. I'll fix up the reply a bit - was 1st coffee when I wrote it
            – Tetsujin
            Aug 31 '14 at 9:58






          • 1




            Awesome. Formatting wise, a sanitised screenshot of the settings page would probably be clearer too
            – Journeyman Geek
            Aug 31 '14 at 11:24










          • Added. Hope it's still useful with that much info blurred out.
            – Tetsujin
            Aug 31 '14 at 11:48
















          Is that a comment, or a suggested set of settings?
          – Journeyman Geek
          Aug 31 '14 at 9:55




          Is that a comment, or a suggested set of settings?
          – Journeyman Geek
          Aug 31 '14 at 9:55












          it's the settings I use on my machine to achieve the same thing. I'll fix up the reply a bit - was 1st coffee when I wrote it
          – Tetsujin
          Aug 31 '14 at 9:58




          it's the settings I use on my machine to achieve the same thing. I'll fix up the reply a bit - was 1st coffee when I wrote it
          – Tetsujin
          Aug 31 '14 at 9:58




          1




          1




          Awesome. Formatting wise, a sanitised screenshot of the settings page would probably be clearer too
          – Journeyman Geek
          Aug 31 '14 at 11:24




          Awesome. Formatting wise, a sanitised screenshot of the settings page would probably be clearer too
          – Journeyman Geek
          Aug 31 '14 at 11:24












          Added. Hope it's still useful with that much info blurred out.
          – Tetsujin
          Aug 31 '14 at 11:48




          Added. Hope it's still useful with that much info blurred out.
          – Tetsujin
          Aug 31 '14 at 11:48












          up vote
          0
          down vote













          It is a bug in Mail; go to Mail, then preferences, then select the account you are having problems with; highlight the outgoing server that does NOT say "offline" then save this setting and try again; worked for me.






          share|improve this answer





















          • Can you clarify what setting to save? It sounds like your instructions don't change anything.
            – fixer1234
            Jan 30 '15 at 5:50















          up vote
          0
          down vote













          It is a bug in Mail; go to Mail, then preferences, then select the account you are having problems with; highlight the outgoing server that does NOT say "offline" then save this setting and try again; worked for me.






          share|improve this answer





















          • Can you clarify what setting to save? It sounds like your instructions don't change anything.
            – fixer1234
            Jan 30 '15 at 5:50













          up vote
          0
          down vote










          up vote
          0
          down vote









          It is a bug in Mail; go to Mail, then preferences, then select the account you are having problems with; highlight the outgoing server that does NOT say "offline" then save this setting and try again; worked for me.






          share|improve this answer












          It is a bug in Mail; go to Mail, then preferences, then select the account you are having problems with; highlight the outgoing server that does NOT say "offline" then save this setting and try again; worked for me.







          share|improve this answer












          share|improve this answer



          share|improve this answer










          answered Jan 30 '15 at 2:59









          Tim

          1




          1












          • Can you clarify what setting to save? It sounds like your instructions don't change anything.
            – fixer1234
            Jan 30 '15 at 5:50


















          • Can you clarify what setting to save? It sounds like your instructions don't change anything.
            – fixer1234
            Jan 30 '15 at 5:50
















          Can you clarify what setting to save? It sounds like your instructions don't change anything.
          – fixer1234
          Jan 30 '15 at 5:50




          Can you clarify what setting to save? It sounds like your instructions don't change anything.
          – fixer1234
          Jan 30 '15 at 5:50


















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