diff --git a/packages/server/postgres/migrations/2025-01-07T19:41:35.458Z_reflectionsToTipTap.ts b/packages/server/postgres/migrations/2025-01-07T19:41:35.458Z_reflectionsToTipTap.ts
new file mode 100644
index 00000000000..edc0720eeba
--- /dev/null
+++ b/packages/server/postgres/migrations/2025-01-07T19:41:35.458Z_reflectionsToTipTap.ts
@@ -0,0 +1,148 @@
+import {generateText, mergeAttributes, type JSONContent} from '@tiptap/core'
+import BaseLink from '@tiptap/extension-link'
+import Mention from '@tiptap/extension-mention'
+import {generateJSON} from '@tiptap/html'
+import StarterKit from '@tiptap/starter-kit'
+import {convertFromRaw, RawDraftContentState} from 'draft-js'
+import {Options, stateToHTML} from 'draft-js-export-html'
+import type {Kysely} from 'kysely'
+
+const serverTipTapExtensions = [
+  StarterKit,
+  Mention.configure({
+    renderText({node}) {
+      return node.attrs.label
+    },
+    renderHTML({options, node}) {
+      return ['span', options.HTMLAttributes, `${node.attrs.label ?? node.attrs.id}`]
+    }
+  }),
+  BaseLink.extend({
+    parseHTML() {
+      return [
+        {
+          tag: 'a[href]:not([data-type="button"]):not([href *= "javascript:" i])'
+        }
+      ]
+    },
+
+    renderHTML({HTMLAttributes}) {
+      return [
+        'a',
+        mergeAttributes(this.options.HTMLAttributes, HTMLAttributes, {
+          class: 'link'
+        }),
+        0
+      ]
+    }
+  })
+]
+
+const getNameFromEntity = (content: RawDraftContentState, userId: string) => {
+  const {blocks, entityMap} = content
+  const entityKey = Number(
+    Object.keys(entityMap).find((key) => entityMap[key]!.data?.userId === userId)
+  )
+  for (let i = 0; i < blocks.length; i++) {
+    const block = blocks[i]!
+    const {entityRanges, text} = block
+    const entityRange = entityRanges.find((range) => range.key === entityKey)
+    if (!entityRange) continue
+    const {length, offset} = entityRange
+    return text.slice(offset, offset + length)
+  }
+  console.log('found unknown for', userId, JSON.stringify(content))
+  return 'Unknown User'
+}
+
+const getTrimmedContent = (content: JSONContent) => {
+  const contentStr = JSON.stringify(content)
+  if (contentStr.length <= 2000) return contentStr
+  const plaintextContent = generateText(content, serverTipTapExtensions)
+  const plainJSONContent = generateJSON(`<p>${plaintextContent}</p>`, serverTipTapExtensions)
+  return JSON.stringify(plainJSONContent)
+}
+
+export const convertKnownDraftToTipTap = (content: RawDraftContentState) => {
+  const contentState = convertFromRaw(content)
+  const options: Options = {
+    entityStyleFn: (entity) => {
+      const entityType = entity.getType().toLowerCase()
+      const data = entity.getData()
+      if (entityType === 'tag') {
+        return {
+          element: 'span',
+          attributes: {
+            'data-id': data.value,
+            'data-type': 'taskTag'
+          }
+        }
+      }
+      if (entityType === 'mention') {
+        const label = getNameFromEntity(content, data.userId)
+        return {
+          element: 'span',
+          attributes: {
+            'data-id': data.userId.toWellFormed(),
+            'data-label': label.toWellFormed(),
+            'data-type': 'mention'
+          }
+        }
+      }
+      return
+    }
+  }
+  const html = stateToHTML(contentState, options)
+  const json = generateJSON(html, serverTipTapExtensions)
+  return json
+}
+
+export async function up(db: Kysely<any>): Promise<void> {
+  let lastId = ''
+
+  for (let i = 0; i < 1e6; i++) {
+    const reflections = await db
+      .selectFrom('RetroReflection')
+      .select(['id', 'content'])
+      .where('id', '>', lastId)
+      .orderBy('id asc')
+      .limit(1000)
+      .execute()
+    console.log('converting reflections', i * 1000)
+    if (reflections.length === 0) break
+    const updatePromises = [] as Promise<any>[]
+    for (const reflection of reflections) {
+      const {id, content: contentStr} = reflection
+      let content
+      try {
+        content = JSON.parse(contentStr)
+      } catch {
+        console.log('invalid json found')
+        continue
+      }
+      if ('blocks' in content) {
+        // this is draftjs
+        const tipTapContent = convertKnownDraftToTipTap(content)
+        const trimmedContentStr = getTrimmedContent(tipTapContent)
+
+        const doPromise = async () => {
+          try {
+            return await db
+              .updateTable('RetroReflection')
+              .set({content: trimmedContentStr})
+              .where('id', '=', id)
+              .execute()
+          } catch (e) {
+            console.log('GOT ERR', id, trimmedContentStr, e)
+            throw e
+          }
+        }
+        updatePromises.push(doPromise())
+      }
+    }
+    await Promise.all(updatePromises)
+    lastId = reflections.at(-1)!.id
+  }
+}
+
+export async function down(db: Kysely<any>): Promise<void> {}