🗞️ Newsletters - Automate the upload flow (use email tool's hosted URL)

[bradystroud]

Background

The newsletter upload flow is still painful for marketing (Penny) three years after it was first flagged. Picking up the thread from a stack of prior issues:

• Newsletters - Upload file feature on TinaCMS #626 — Newsletters - Upload file feature on TinaCMS (Gilles, May 2023, closed by Harry's ✨Newsletters - File Upload on TinaCMS #821)
• 📄🎥 Newsletters - How to upload? #712 — 📄🎥 Newsletters - How to upload? (Brady, Jul 2023, still OPEN; Harry recorded the demo video below)
• ✨Newsletters - File Upload on TinaCMS #821 — ✨Newsletters - File Upload on TinaCMS (Harry, shipped the Tina upload UI)
• 🐛 Newsletter wont upload to Tina #1070 — 🐛 Newsletter wont upload to Tina (Penny, still OPEN)

📺 Harry's demo video for Penny: https://youtu.be/lrgF3T7Y0Qs

📝 Full findings doc (in branch chore/pin-and-update-deps): _docs/NEWSLETTER_AUTOMATION_FINDINGS.md (will land in its own PR)

Adam's feedback on #712 already pointed at the right answer two years ago: "Now you would send it with MailChimp or Campaign Monitor or Sendgrid?" — yes, exactly that.

Current process

1. Marketing edits an HTML template (hand-coded, <!-- EDIT HERE --> markers)
2. Save as _YYYY_MM__Title__.html (rigid underscore convention)
3. Upload into public/images/newsletter-uploads/<YYYY>/
4. Run scripts/fix_newsletter_images.py (rewrites case-mismatched <img> paths)
5. Run scripts/fix-newsletter-titles.py (needs Azure AI credentials to de-dupe <title> tags)
6. Open Tina /admin → add row to content/newsletters/_<YYYY>.json (month, file path, description)
7. Commit / PR / deploy
8. Send the actual email via Dynamics 365 (Customer Insights – Journeys) — repo isn't even the source of truth for the sent email

Pain points

• Brittle filename convention; easy to break
• content/newsletters/_2025.json line 31 has %2520 (double-encoded space) from manual entry
• Description drifts across three places (JSON / filename / <title>) — Mar 2025 says "Why Rules are Cool" in JSON but the filename says "…The Secret to Smarter Teams"
• Two Python scripts a non-dev must run locally; one needs Azure AI credentials
• No append helper — _2025.json has months in random order
• HTML template authoring with <!-- EDIT HERE --> markers is itself a friction point upstream
• Tina upload was supposed to fix this (✨Newsletters - File Upload on TinaCMS #821) but failed for Penny (🐛 Newsletter wont upload to Tina #1070); the issue was never closed

Why all this exists

We're hosting a second copy of an email that's already authored, stored, and hosted by Dynamics 365. Every major email tool — Dynamics 365 Customer Insights, Mailchimp, Campaign Monitor, HubSpot, Brevo — produces a permanent public "view in browser" URL per campaign. Storing that URL in Tina (instead of a hand-crafted HTML file) collapses steps 1–6 above.

Recommended path

Path 1 — Use the email tool's archive URL (smallest, fastest):

- file:        image upload   (HTML, requires fix-up scripts)
+ archiveUrl:  string         (paste the "view in browser" URL after sending)

NewslettersTable renders <a href={archiveUrl} target="_blank"> per row. Existing newsletters stay as static files in /newsletter-uploads/; schema accepts both file and archiveUrl during migration.

• Cost: ~½ day dev work
• Friction per newsletter after: ~5 seconds (paste one URL)
• Blocker: confirm Dynamics produces a stable public archive URL per campaign

If marketing is open to migrating away from hand-coded HTML, Path 2 (move sending to Mailchimp's drag-and-drop editor, then Path 1) is the better long-term answer. Adam suggested this in 2023.

Cleanup to bundle into the same PR (whichever path)

• Fix the %2520 double-encoding bug in _2025.json (Feb entry)
• Decide whether description is source-of-truth in JSON or derived from the HTML/campaign subject
• Document the kept-or-killed status of scripts/fix_newsletter_images.py and scripts/fix-newsletter-titles.py
• Close 📄🎥 Newsletters - How to upload? #712 and 🐛 Newsletter wont upload to Tina #1070 as resolved-by-this-issue (or roll their tasks in)

Open questions for Adam / marketing

1. Confirm the email tool is Dynamics 365 Customer Insights – Journeys.
2. Does each Dynamics campaign produce a public "view as web page" URL we can link to?
3. Any policy reason the newsletter HTML must live on ssw.com.au rather than the email tool's domain? (SEO: could mitigate with a redirect ssw.com.au/newsletters/2025/07 → archive URL.)
4. Keep existing /images/newsletter-uploads/... URLs live forever? (Yes by default — archive integrity.)

cc @adamcogan @PennyWalker

[bradystroud]

Existing wiki doc: https://github.com/SSWConsulting/SSW.Website/wiki/Editing-the-website#adding-new-newsletters

The wiki has the documented happy-path (Harry's video is embedded — same https://youtu.be/lrgF3T7Y0Qs link), last edited by Eli Kent on 2026-01-07. Worth noting:

• The wiki steps do not mention scripts/fix_newsletter_images.py or scripts/fix-newsletter-titles.py — suggesting they're a dev-only fallback when the HTML import goes sideways, not part of Penny's documented workflow.
• The wiki workflow ends at "Click Save → create a PR". It assumes Tina upload works — i.e. it doesn't cover 🐛 Newsletter wont upload to Tina #1070 (Penny's "won't upload" bug).

So the actual support matrix is:

Path	Documented?	Works for Penny?
Tina upload (wiki)	✅ wiki + video	❌ #1070 still open
Python scripts fallback	❌ undocumented	n/a — dev only
Path 1 (archive URL) — proposed here	TBD	should — 5 sec paste-one-URL

When Path 1 lands, the wiki section needs a rewrite to match.