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[ Updated on 2 August 2015 ]
ISSUE: Email sent to Hotmail or Gmail goes to junk/spam folder.
POSSIBLE REASONS:
1) IP not set with proper SPF or PTR records.
2) IP is blacklisted and has been classifed as spamming IP.
3) High volume of emails goes to Hotmail /Gmail server from IP or source that has been classified by Hotmail/Gmail users as Junk or Spam mail.
If any of the IPs were previously blacklisted, Gmail and Hotmail filtering system may need some time (estimate about 3-7 days) establish that your email sends out legitimate emails.
Please request Gmail/Hotmail user (recipient) to mark your emails as Not Junk or Spam for spam filtering system to learn your email is not junk or spam faster.
For more information, you can check the following links:
Hotmail: [ http://mail.live.com/mail/junkemail.aspx ] --> SmartScreen
Gmail: [ https://support.google.com/mail/answer/81126 ] --> "Delivery"
KB: [ http://gmailblog.blogspot.com/2012/03/learn-why-message-ended-up-in-your-spam.html ]
To prevent emails from landing in Microsoft Outlook's Junk Folder, you may refer to this KB article.
For Hotmail Users - emails still land in Junk Folder during IP Mitigation period or after IP blacklisting issue is resolved:
Kindly take note that Hotmail IP Mitigation period will take place for 2 days (48 hours). During this period, the emails may land in Hotmail user's junk folder.
Users are advised to click on "Not Junk" option in the mentioned email folder to prevent the emails from landing in junk folder in the future as well as to speed up the mitigation process.
See screenshot below - "Not Junk" option:
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