Mac Mail - multiple hotmail accounts, only 1 works

In my Mac mail I have 2 separate Hotmail addresses identically set-up following the instructions widely available.
The 1 email works perfectly and the other fails to sync, it just times out. I captured the logs and the failing account does not even get by step 1 in attempting to reach the Hotmail server. Eventually it will just time out.
Ive tried resetting my Mac Mail, Redoing the accounts from scratch, but this problem persists itself.

Try deleting the account and adding it back.
Troubleshooting Apple Mail
What does Mail/Window/Connection Doctor Show? If the server is red, select it and look at the Show Details box.
Troubleshooting sending and receiving email messages
Troubleshooting sending email messages
SMTP servers keep going offline

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    Problem description:
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    EtreCheck version: 2.0.11 (98)
    Report generated 1 December 2014 16:51:49 CET
    Hardware Information: ℹ️
      iMac (21.5-inch, Late 2009) (Verified)
      iMac - model: iMac10,1
      1 3.06 GHz Intel Core 2 Duo CPU: 2-core
      12 GB RAM Upgradeable
      BANK 0/DIMM0
      4 GB DDR3 1067 MHz ok
      BANK 1/DIMM0
      4 GB DDR3 1067 MHz ok
      BANK 0/DIMM1
      2 GB DDR3 1067 MHz ok
      BANK 1/DIMM1
      2 GB DDR3 1067 MHz ok
      Bluetooth: Old - Handoff/Airdrop2 not supported
      Wireless:  en1: 802.11 a/b/g/n
    Video Information: ℹ️
      NVIDIA GeForce 9400 - VRAM: 256 MB
      iMac 1920 x 1080
      BenQ GL2240 1920 x 1080 @ 60 Hz
    System Software: ℹ️
      OS X 10.9.5 (13F34) - Uptime: 1:32:17
    Disk Information: ℹ️
      WDC WD5000AAKS-40V2B0 disk0 : (500.11 GB)
      S.M.A.R.T. Status: Verified
      EFI (disk0s1) <not mounted> : 210 MB
      Macintosh HD (disk0s2) /  [Startup]: 499.25 GB (164.03 GB free)
      Recovery HD (disk0s3) <not mounted>  [Recovery]: 650 MB
      HL-DT-ST DVDRW  GA11N 
    USB Information: ℹ️
      EPSON EPSON Epson Stylus S22 Series
      Canon MX410 series
      ASMedia AS2105 1 TB
      S.M.A.R.T. Status: Verified
      EFI (disk3s1) <not mounted> : 210 MB
      Backup (disk3s2) /Volumes/Backup : 999.86 GB (506.24 GB free)
      Apple Inc. Built-in iSight
      Apple Internal Memory Card Reader 7.95 GB
      S.M.A.R.T. Status: Verified
      EOS_DIGITAL (disk1s1) /Volumes/EOS_DIGITAL : 7.94 GB (7.83 GB free)
      Western Digital My Book 1140 2 TB
      S.M.A.R.T. Status: Verified
      EFI (disk2s1) <not mounted> : 210 MB
      2TB (disk2s2) /Volumes/2TB : 2.00 TB (1.50 TB free)
      Wacom Co.,Ltd. CTE-450
      Contour Design ShuttlePRO v2
      Apple Computer, Inc. IR Receiver
      Apple Inc. BRCM2046 Hub
      Apple Inc. Bluetooth USB Host Controller
    Gatekeeper: ℹ️
      Mac App Store and identified developers
    Kernel Extensions: ℹ️
      /Applications/Parallels Desktop.app
      [not loaded] com.parallels.kext.hidhook (9.0 24217.979618) Support
      [not loaded] com.parallels.kext.hypervisor (9.0 24217.979618) Support
      [not loaded] com.parallels.kext.netbridge (9.0 24217.979618) Support
      [not loaded] com.parallels.kext.usbconnect (9.0 24217.979618) Support
      [not loaded] com.parallels.kext.vnic (9.0 24217.979618) Support
      /Applications/Toast 10 Titanium/Toast Titanium.app
      [not loaded] com.roxio.BluRaySupport (1.1.6) Support
      /Library/Extensions
      [loaded] at.obdev.nke.LittleSnitch (4052 - SDK 10.8) Support
      [not loaded] xxx.qnation.PeerGuardian (1.1.9) Support
      /System/Library/Extensions
      [not loaded] com.FTDI.driver.FTDIUSBSerialDriver (2.2.18 - SDK 10.6) Support
      [not loaded] com.pctools.iantivirus.kfs (1.0.1) Support
      /Users/[redacted]/Library/Services/ToastIt.service/Contents/MacOS
      [not loaded] com.roxio.TDIXController (2.0) Support
    Startup Items: ℹ️
      ParallelsDesktopTransporter: Path: /Library/StartupItems/ParallelsDesktopTransporter
      WkSvMacX: Path: /Library/StartupItems/WkSvMacX
      Startup items are obsolete and will not work in future versions of OS X
    Launch Agents: ℹ️
      [running] at.obdev.LittleSnitchUIAgent.plist Support
      [not loaded] com.adobe.AAM.Updater-1.0.plist Support
      [loaded] com.adobe.CS4ServiceManager.plist Support
      [running] com.epson.epw.agent.plist Support
      [loaded] com.oracle.java.Java-Updater.plist Support
    Launch Daemons: ℹ️
      [running] at.obdev.littlesnitchd.plist Support
      [failed] com.adobe.fpsaud.plist Support
      [loaded] com.adobe.versioncueCS4.plist Support
      [loaded] com.barebones.textwrangler.plist Support
      [running] com.cleverfiles.cfbackd.plist Support
      [not loaded] com.gopro.stereomodestatus.plist Support
      [loaded] com.microsoft.office.licensing.helper.plist Support
      [loaded] com.oracle.java.Helper-Tool.plist Support
      [loaded] com.oracle.java.JavaUpdateHelper.plist Support
      [invalid?] com.tvmobili.tvmobilisvcd.plist Support
      [loaded] fi.polar.libpolar.plist Support
      [running] fi.polar.polard.plist Support
      [failed] xxx.qnation.PeerGuardian.kextload.plist Support
    User Launch Agents: ℹ️
      [loaded] com.adobe.ARM.[...].plist Support
      [loaded] com.facebook.videochat.[redacted].plist Support
      [loaded] com.google.keystone.agent.plist Support
      [loaded] com.macpaw.CleanMyMac.helperTool.plist Support
      [loaded] com.macpaw.CleanMyMac.trashSizeWatcher.plist Support
      [running] com.macpaw.CleanMyMac.volumeWatcher.plist Support
      [invalid?] com.plexapp.helper.plist Support
      [not loaded] com.spotify.webhelper.plist Support
    User Login Items: ℹ️
      Garmin Express Service Application (/Applications/Garmin Express.app/Contents/Library/LoginItems/Garmin Express Service.app)
      SmartDaemon Application (/Library/Application Support/CleverFiles/SmartDaemon.app)
      SilverKeeper Scheduler ApplicationHidden (/Applications/SilverKeeper.app/Contents/Resources/SilverKeeper Scheduler.app)
      Dropbox Application (/Applications/Dropbox.app)
      Garmin ANT Agent UNKNOWN (missing value)
    Internet Plug-ins: ℹ️
      DirectorShockwave: Version: 11.5.7r609 Support
      Google Earth Web Plug-in: Version: 6.1 Support
      Default Browser: Version: 537 - SDK 10.9
      Flip4Mac WMV Plugin: Version: 3.2.0.16   - SDK 10.8 Support
      PandoWebInst: Version: 1.0 Support
      AdobePDFViewerNPAPI: Version: 10.1.12 Support
      FlashPlayer-10.6: Version: 15.0.0.189 - SDK 10.6 Support
      DivXBrowserPlugin: Version: 2.0 Support
      Silverlight: Version: 5.1.10411.0 - SDK 10.6 Support
      Flash Player: Version: 15.0.0.189 - SDK 10.6 Mismatch! Adobe recommends 15.0.0.239
      iPhotoPhotocast: Version: 7.0 - SDK 10.8
      QuickTime Plugin: Version: 7.7.3
      SharePointBrowserPlugin: Version: 14.0.0 Support
      AdobePDFViewer: Version: 10.1.12 Support
      GarminGpsControl: Version: 4.2.0.0 - SDK 10.8 Support
      JavaAppletPlugin: Version: Java 7 Update 71 Check version
    User Internet Plug-ins: ℹ️
      fbplugin_1_0_3: Version: (null) Support
    Safari Extensions: ℹ️
      Open in Internet Explorer
    Audio Plug-ins: ℹ️
      DVCPROHDAudio: Version: 1.3.2
    3rd Party Preference Panes: ℹ️
      Adobe Version Cue CS4  Support
      DivX  Support
      Flash Player  Support
      Flip4Mac WMV  Support
      GoPro  Support
      Growl  Support
      Java  Support
      MacFUSE  Support
      MenuMeters  Support
      Perian  Support
    Time Machine: ℹ️
      Skip System Files: NO
      Auto backup: NO - Auto backup turned off
      Destinations:
      Back Up [Local]
      Total size: 0 B
      Total number of backups: 0
      Oldest backup: -
      Last backup: -
      Size of backup disk: Excellent
      Backup size 0 B > (Disk size 0 B X 3)
    Top Processes by CPU: ℹ️
          12% Google Chrome
          12% WindowServer
          4% Dock
          2% Little Snitch Agent
          2% SystemUIServer
    Top Processes by Memory: ℹ️
      399 MB iTunes
      322 MB mds_stores
      216 MB Google Chrome Helper
      193 MB Google Chrome
      155 MB com.apple.IconServicesAgent
    Virtual Memory Information: ℹ️
      6.64 GB Free RAM
      3.51 GB Active RAM
      1.36 GB Inactive RAM
      1.11 GB Wired RAM
      1.91 GB Page-ins
      0 B Page-outs

      [not loaded] com.pctools.iantivirus.kfs (1.0.1) Support
    Un-install according to the developer's un-install instructions.
    You do not need to use cleaning programs. They can destroy your computer operation as they may already have done.
    CleanMyMac - Uninstall
    CleanMyMac2 Un-install
    After un-installing, run this program to make sure you got all the pieces.
    EasyFind – Spotlight Replacement
    Do a backup.
    Go to Finder and select your user/home folder. With that Finder window as the front window, either select Finder/View/Show View options or go command - J.  When the View options opens, check ’Show Library Folder’. That should make your user library folder visible in your user/home folder.  Select Library. Then go to Preferences/com.apple.appstore.plist. Move the .plist to your desktop.
    Restart, open the application and test. If it works okay, delete the plist from the desktop.
    If the application is the same, return the .plist to where you got it from, overwriting the newer one.
    Thanks to leonie for some information contained in this.

  • My hotmail account is not working on my imac, but does work on pc

    For some reason my hotmail account is not working on my Imac but it is on my Ipad and another pc. Does anyone have an idea what may be wrong?
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    I have a simmilar issue with my iPhone over Safari, refresh, reply, forward etc just don't work !

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  • Can I get my hotmail in Mac Mail?? (httpmail no longer works)

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    Occam's Razor nearly always applies when troubleshooting technology issues!
    If anyone has been helpful to you, please show your appreciation by clicking the button inside of their post. Please click here and read, along with the threads to which it links, for helpful information to guide you as you proceed. I always recommend that you treat your BlackBerry like any other computing device, including using a regular backup schedule...click here for an article with instructions.
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  • Multiple hotmail accounts but one will not send mails and gives no error messages

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    This problem in Mail is usually caused by some Launch Services cache or preferences corruption that affects the built-in spell checker. The following article describes how to manually reset Launch Services — the notes at the bottom of the article also provide information about the side effects of deleting each of the files involved:
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