An honest comparison
Pinpress vs Tailwind
Tailwind schedules the pins you make. Pinpress makes the pins — then schedules and posts them for you. Here's the full picture, competitor strengths included.
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Pins generated by Pinpress — no design tool involved.
The short version
Tailwind is a social media scheduler: you design pins (or assemble them from templates in Tailwind Create), and it publishes them to Pinterest, Instagram and Facebook at optimal times. Pinpress automates the step Tailwind leaves to you — it watches your blog, generates the pin designs itself, and schedules and posts them. Pick Tailwind if you want one tool for three networks. Pick Pinpress if you want Pinterest traffic from your blog without making creatives.
The workflow
What publishing a post looks like
Both tools post to Pinterest. The difference is everything that happens before the post.
With Tailwind
You do the work- 1 Write and publish the post
- 2 Design pins in Tailwind Create or Canva
- 3 Write the titles and descriptions
- 4 Add each pin to the queue
- 5 Review the SmartSchedule slots
- 6 Tailwind posts at the scheduled time
Repeat for every post — and every back-catalog post you want repinned.
With Pinpress
Automated- 1 Write and publish the post
- Pinpress spots it on your sitemap
- Generates pin designs in your brand colors
- Writes the overlay copy, titles and descriptions
- Schedules and posts, spaced across your boards
Step 1 is your whole job. Your back catalog gets the same treatment.
Side by side
At a glance
| Pinpress | Tailwind | |
|---|---|---|
| Core job | Creates and schedules pins from your blog, automatically | Schedules content you create; templates speed up design |
| Networks | Pinterest only | Pinterest, Instagram, Facebook |
| Pin design | AI-generated from your URL — brand colors, your post images, written overlay copy | Tailwind Create templates — you assemble and approve each design |
| New-post detection | Automatic — watches your sitemap and picks up every new post | Manual — you add each post to the queue |
| Scheduling | Automatic optimal-time slots with board-aware spacing | SmartSchedule optimal-time slots |
| Accounts per plan | Unlimited Pinterest accounts | 1 (Pro), 2 (Advanced), 3 (Max) |
| Free option | 7-day free trial | Free plan — 5 posts/month |
| Starting price | $12/mo billed annually ($144/yr), or $15 month-to-month | Pro: $17.99/mo billed annually ($29.99 month-to-month) |
Tailwind details verified from their pricing page on July 14, 2026. Prices shown are annual-billing rates; check their site for current figures.
The details
How they actually differ
The core difference: who makes the pins
Tailwind assumes the creative already exists. Its job is to take pins you've designed — in Canva, in Photoshop, or in its own Tailwind Create template tool — and publish them at the right times. Tailwind Create genuinely speeds design up, but you still pick a template, review every variation, and approve each pin. Pinpress starts one step earlier: you point it at a blog post (or connect your sitemap), and it scrapes the content, extracts your brand colors and the post's own images, writes the overlay copy, and produces finished pin designs. Design stops being a task on your list at all.
Bottom line: If you enjoy designing pins or need pixel control, Tailwind keeps you in the driver's seat. If pin design is the chore you're trying to delete, that's the job Pinpress was built for.
Running Pinterest every day
Pinterest rewards consistent, fresh pinning — which is why both tools exist. With Tailwind, consistency means keeping the queue fed: every new blog post is a trip through design and scheduling. With Pinpress, publishing the blog post is the whole workflow — it detects the new URL from your sitemap, checks the page actually suits Pinterest, generates the pins, and spaces them across your boards so the account stays active without looking like spam. It will also work through your back catalog, turning old posts into fresh pins.
Bottom line: Tailwind automates posting. Pinpress automates the pipeline that feeds the posting.
Beyond Pinterest
This one is simply Tailwind's win. Tailwind publishes to Pinterest, Instagram and Facebook from one queue, and its plans bundle cross-network analytics and monthly AI credits for caption writing. Pinpress does not post to Instagram or Facebook and has no plans dressed up to pretend otherwise — it is a Pinterest traffic machine for content sites, full stop.
Bottom line: Need one tool for three networks? Use Tailwind — or use both tools for what each does best.
Pricing
Tailwind's paid plans (billed annually) are Pro at $17.99/mo with 150 posts and 150 AI credits a month on one account, Advanced at $29.99/mo with 300 posts across two accounts, and Max at $49.99/mo with unlimited posts across three accounts. Month-to-month, those jump to $29.99, $54.99 and $99.99. There's also a real free plan capped at 5 posts a month. Pinpress has one plan: $12/mo billed annually or $15 month-to-month, with 50 pin-generation credits a month, unlimited Pinterest accounts, and top-up credit packs when you need more. Like-for-like — Pinterest automation for one site — Pinpress costs less than Tailwind Pro and includes the design work Tailwind leaves to you.
Bottom line: Tailwind charges for posting volume across networks; Pinpress charges for pins created. If Pinterest is the goal, the Pinpress plan is both cheaper and more complete.
The verdict
Which one is for you?
Choose Pinpress if…
- Bloggers and niche-site owners who want Pinterest as a traffic channel, not another job
- Sites with a back catalog — hundreds of old posts become fresh pins automatically
- Anyone without a designer or VA in the loop (or who wants Canva evenings back)
- Agencies managing several Pinterest accounts — unlimited accounts on one plan
Choose Tailwind if…
- You post to Instagram and Facebook as much as Pinterest and want one queue
- You like designing pins and want template tooling, not full automation
- You want a forever-free plan to start on (5 posts/month)
- You use Tailwind Communities to swap distribution with other creators
Honest answer: some teams should use both — Tailwind for the networks Pinpress doesn't touch, Pinpress for Pinterest on autopilot.
FAQ
Common questions
Still weighing it up? These come up most. Anything else, ask us directly.
Contact support →Can I use Pinpress and Tailwind together?
Do I need to migrate anything from Tailwind?
Does Pinpress post to Instagram or Facebook?
Will automated pinning get my account banned?
See your blog as Pinterest pins
Connect your site, and Pinpress generates your first pin designs from posts you've already written.
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