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Font Awesome shares their experience with Gmail's email deliverability black hole despite having a 99% sender reputation in SendGrid. Gmail runs its own independent reputation system, and their emails were silently landing in spam folders. The post explains a core catch-22 of email deliverability: sending too infrequently to respect users' inboxes causes IP warmth to drop, while sending too often generates spam complaints. They're working on fixes including list culling and slower send cadences, and use the post to also promote their new Build Awesome Kickstarter campaign.