diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/image-paste.test.ts b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/image-paste.test.ts
index 766e4c77ef6..d782141e81c 100644
--- a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/image-paste.test.ts
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/image-paste.test.ts
@@ -1,8 +1,36 @@
 /**
  * @vitest-environment jsdom
  */
-import { describe, expect, it } from 'vitest'
-import { extractImageFiles } from './image-paste'
+import { Editor } from '@tiptap/core'
+import { beforeEach, describe, expect, it, vi } from 'vitest'
+import { extractEmbeddedFileRef } from '@/lib/uploads/utils/embedded-image-ref'
+import {
+  createPublicFileContentSource,
+  createWorkspaceFileContentSource,
+} from '@/hooks/use-file-content-source'
+import { createMarkdownEditorExtensions } from './editor-extensions'
+import {
+  extractImageFiles,
+  extractImgSrcs,
+  findHostedImageAttrs,
+  hasHostedImageHtml,
+  isInlineRouteSrc,
+  shouldSkipFileUpload,
+} from './image-paste'
+
+// jsdom lacks `elementFromPoint`; the Placeholder extension's viewport tracking calls it on mount.
+beforeEach(() => {
+  vi.stubGlobal(
+    'ResizeObserver',
+    class {
+      observe() {}
+      unobserve() {}
+      disconnect() {}
+    }
+  )
+  Element.prototype.scrollIntoView = vi.fn()
+  document.elementFromPoint = vi.fn(() => null)
+})
 
 function imageFile(name = 'shot.png'): File {
   return new File([''], name, { type: 'image/png' })
@@ -54,3 +82,209 @@ describe('extractImageFiles', () => {
     expect(result).toEqual([])
   })
 })
+
+describe('hasHostedImageHtml', () => {
+  const isHosted = (src: string) => src.startsWith('/api/files/view/')
+
+  it('detects an <img> whose src is recognized as one of our own hosted files', () => {
+    expect(hasHostedImageHtml('<img src="/api/files/view/wf_abc" alt="x">', isHosted)).toBe(true)
+  })
+
+  it('is false when the html has no img, or the img src is not one of ours', () => {
+    expect(hasHostedImageHtml('<p>hello</p>', isHosted)).toBe(false)
+    expect(hasHostedImageHtml('<img src="https://other-site.com/photo.jpg">', isHosted)).toBe(false)
+    expect(hasHostedImageHtml('', isHosted)).toBe(false)
+  })
+
+  it('matches a hosted img among multiple candidates', () => {
+    expect(
+      hasHostedImageHtml(
+        '<img src="https://other-site.com/a.png"><img src="/api/files/view/wf_abc">',
+        isHosted
+      )
+    ).toBe(true)
+  })
+
+  // Regression: the browser doesn't put the node's persisted `attrs.src` (`/api/files/view/...`)
+  // onto the clipboard when a rendered <img> is copied — it puts the actual DOM `src`, which is
+  // `resolveImageSrc`'s REWRITTEN display URL (`/…/files/inline?key=…`/`?fileId=…`). A predicate
+  // that only recognizes the persisted shape (as `extractEmbeddedFileRef` alone does) never matches
+  // a real same-page copy, silently falling through to the re-upload path it exists to avoid.
+  it('recognizes the real rendered <img src> end-to-end, not just the persisted reference shape', () => {
+    const ws = createWorkspaceFileContentSource('ws-1')
+    const renderedFromKey = ws.resolveImageSrc(
+      '/api/files/serve/workspace/ws-1/1700000000000-deadbeefdeadbeef-photo.png'
+    )
+    const renderedFromFileId = ws.resolveImageSrc('/api/files/view/wf_abc')
+    expect(renderedFromKey).toMatch(/^\/api\/workspaces\/ws-1\/files\/inline\?key=/)
+    expect(renderedFromFileId).toBe('/api/workspaces/ws-1/files/inline?fileId=wf_abc')
+
+    // extractEmbeddedFileRef alone (the persisted-content recognizer) does NOT match either
+    // rendered form — that's the exact gap isInlineRouteSrc closes.
+    expect(extractEmbeddedFileRef(renderedFromKey as string)).toBeNull()
+    expect(extractEmbeddedFileRef(renderedFromFileId as string)).toBeNull()
+
+    const isHostedReal = (src: string) => extractEmbeddedFileRef(src) !== null
+    expect(hasHostedImageHtml(`<img src="${renderedFromKey}">`, isHostedReal)).toBe(true)
+    expect(hasHostedImageHtml(`<img src="${renderedFromFileId}">`, isHostedReal)).toBe(true)
+  })
+
+  it('recognizes the public-share inline route too', () => {
+    const pub = createPublicFileContentSource('tok_1', '/api/files/public/tok_1/content')
+    const rendered = pub.resolveImageSrc('/api/files/view/wf_abc')
+    expect(rendered).toBe('/api/files/public/tok_1/inline?fileId=wf_abc')
+    expect(hasHostedImageHtml(`<img src="${rendered}">`, () => false)).toBe(true)
+  })
+
+  it('matches a valid unquoted src attribute (unquoted attribute values are valid HTML)', () => {
+    expect(hasHostedImageHtml('<img src=/api/files/view/wf_abc>', isHosted)).toBe(true)
+    expect(hasHostedImageHtml("<img alt='x' src=/api/files/view/wf_abc alt=y>", isHosted)).toBe(
+      true
+    )
+    expect(hasHostedImageHtml('<img src=https://other-site.com/a.png>', isHosted)).toBe(false)
+  })
+
+  it('matches single-quoted src attributes too', () => {
+    expect(hasHostedImageHtml("<img src='/api/files/view/wf_abc'>", isHosted)).toBe(true)
+  })
+})
+
+describe('extractImgSrcs', () => {
+  it('extracts every img src in document order, including duplicates', () => {
+    expect(
+      extractImgSrcs('<img src="/a.png"><p>text</p><img src="/b.png"><img src="/a.png">')
+    ).toEqual(['/a.png', '/b.png', '/a.png'])
+  })
+
+  it('returns an empty array for html with no img', () => {
+    expect(extractImgSrcs('<p>hello</p>')).toEqual([])
+    expect(extractImgSrcs('')).toEqual([])
+  })
+})
+
+describe('shouldSkipFileUpload (shared by paste and drop)', () => {
+  const isHosted = (src: string) => src.startsWith('/api/files/view/')
+  const hostedHtml = '<img src="/api/files/view/wf_abc">'
+
+  it('skips upload for a single already-hosted image', () => {
+    expect(shouldSkipFileUpload([imageFile()], hostedHtml, isHosted)).toBe(true)
+  })
+
+  it('does not skip when there is no html, or the html is not one of ours', () => {
+    expect(shouldSkipFileUpload([imageFile()], '', isHosted)).toBe(false)
+    expect(shouldSkipFileUpload([imageFile()], '<img src="https://x.com/a.png">', isHosted)).toBe(
+      false
+    )
+  })
+
+  it('does not skip when there are no files to upload in the first place', () => {
+    expect(shouldSkipFileUpload([], hostedHtml, isHosted)).toBe(false)
+  })
+
+  // Regression: a genuinely mixed paste/drop (the hosted image plus a separate new one) must
+  // still upload the new file — bailing out entirely here would silently drop it.
+  it('does not skip a mixed paste/drop carrying more than one image file', () => {
+    expect(
+      shouldSkipFileUpload([imageFile('a.png'), imageFile('b.png')], hostedHtml, isHosted)
+    ).toBe(false)
+  })
+
+  // Regression: this must be content-based (the accompanying html), not keyed off any mutable
+  // per-drag flag like ProseMirror's `view.dragging` — that flag can go briefly stale (cleared up
+  // to ~50ms late via `dragend` when a prior internal drag was dropped outside the view), and a
+  // flag-based check would incorrectly suppress upload of an unrelated new file dropped in that
+  // window. This function only reacts to what THIS specific event's `html`/`images` contain.
+  it('is a pure function of the images/html actually offered, independent of any drag-session flag', () => {
+    expect(shouldSkipFileUpload([imageFile()], '', isHosted)).toBe(false)
+    expect(shouldSkipFileUpload([imageFile()], hostedHtml, isHosted)).toBe(true)
+  })
+})
+
+describe('isInlineRouteSrc', () => {
+  it('recognizes the workspace- and public-scoped inline route with key or fileId', () => {
+    expect(isInlineRouteSrc('/api/workspaces/ws-1/files/inline?key=workspace%2Fws-1%2Fa.png')).toBe(
+      true
+    )
+    expect(isInlineRouteSrc('/api/workspaces/ws-1/files/inline?fileId=wf_abc')).toBe(true)
+    expect(isInlineRouteSrc('/api/files/public/tok_1/inline?fileId=wf_abc')).toBe(true)
+  })
+
+  it('rejects non-inline paths, unrecognized query params, and external/absolute origins', () => {
+    expect(isInlineRouteSrc('/api/files/serve/workspace/ws-1/a.png')).toBe(false)
+    expect(isInlineRouteSrc('/api/workspaces/ws-1/files/inline')).toBe(false)
+    expect(isInlineRouteSrc('/api/workspaces/ws-1/files/inline?other=1')).toBe(false)
+    expect(isInlineRouteSrc('https://other-site.com/files/inline?key=x')).toBe(false)
+    expect(isInlineRouteSrc('data:image/png;base64,aaaa')).toBe(false)
+  })
+})
+
+describe('findHostedImageAttrs', () => {
+  const ws = createWorkspaceFileContentSource('ws-1')
+
+  function docWithImages(...attrs: Array<Record<string, unknown>>): Editor {
+    return new Editor({
+      extensions: createMarkdownEditorExtensions({ placeholder: '' }),
+      content: {
+        type: 'doc',
+        content: attrs.map((a) => ({ type: 'image', attrs: a })),
+      },
+    })
+  }
+
+  // Regression: this is the exact mechanism that avoids persisting the display-layer inline URL
+  // (Cursor's "Paste persists display image URLs" finding) — cloning the REAL node's attrs rather
+  // than re-deriving a node from the clipboard html's rewritten src.
+  it('finds the existing node whose RESOLVED (display) src matches, and returns its REAL persisted attrs', () => {
+    const persistedSrc = '/api/files/view/wf_abc'
+    const editor = docWithImages({ src: persistedSrc, alt: 'photo', width: '300' })
+    const renderedSrc = ws.resolveImageSrc(persistedSrc) as string
+    expect(renderedSrc).not.toBe(persistedSrc) // sanity: the rendered form really differs
+
+    const match = findHostedImageAttrs(editor.state.doc, [renderedSrc], ws.resolveImageSrc)
+    expect(match).not.toBeNull()
+    expect(match?.src).toBe(persistedSrc) // the REAL persisted src, not the rendered one
+    expect(match?.alt).toBe('photo')
+    expect(match?.width).toBe('300')
+  })
+
+  it('returns null when no node in the doc resolves to any target src', () => {
+    const editor = docWithImages({ src: '/api/files/view/wf_other' })
+    const match = findHostedImageAttrs(
+      editor.state.doc,
+      ['/api/workspaces/ws-1/files/inline?fileId=wf_abc'],
+      ws.resolveImageSrc
+    )
+    expect(match).toBeNull()
+  })
+
+  it('returns null for an empty doc or an empty target list', () => {
+    const editor = docWithImages()
+    expect(findHostedImageAttrs(editor.state.doc, ['/anything'], ws.resolveImageSrc)).toBeNull()
+    const editorWithImage = docWithImages({ src: '/api/files/view/wf_abc' })
+    expect(findHostedImageAttrs(editorWithImage.state.doc, [], ws.resolveImageSrc)).toBeNull()
+  })
+
+  it('matches the first of several images, not just the last', () => {
+    const editor = docWithImages(
+      { src: '/api/files/view/wf_one', alt: 'one' },
+      { src: '/api/files/view/wf_two', alt: 'two' }
+    )
+    const renderedTwo = ws.resolveImageSrc('/api/files/view/wf_two') as string
+    const match = findHostedImageAttrs(editor.state.doc, [renderedTwo], ws.resolveImageSrc)
+    expect(match?.alt).toBe('two')
+  })
+
+  it('returns a defensive copy, not a live reference to the node attrs object', () => {
+    const persistedSrc = '/api/files/view/wf_abc'
+    const editor = docWithImages({ src: persistedSrc, alt: 'photo' })
+    const renderedSrc = ws.resolveImageSrc(persistedSrc) as string
+    const match = findHostedImageAttrs(editor.state.doc, [renderedSrc], ws.resolveImageSrc)
+    expect(match).not.toBeNull()
+    if (match) match.alt = 'mutated'
+    let originalAlt: unknown
+    editor.state.doc.descendants((node) => {
+      if (node.type.name === 'image') originalAlt = node.attrs.alt
+    })
+    expect(originalAlt).toBe('photo')
+  })
+})
diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/image-paste.ts b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/image-paste.ts
index ff72fededf9..d3bc170f317 100644
--- a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/image-paste.ts
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/image-paste.ts
@@ -12,3 +12,121 @@ export function extractImageFiles(transfer: DataTransfer | null): File[] {
     .map((item) => item.getAsFile())
     .filter((file): file is File => file !== null)
 }
+
+// `src` may be double-quoted, single-quoted, or (validly) unquoted per the HTML spec — the browser's
+// own clipboard serialization always quotes it, but other producers of `text/html` are not obligated
+// to.
+const IMG_SRC_RE = /<img\b[^>]*\bsrc\s*=\s*(?:"([^"]*)"|'([^']*)'|([^\s"'>]+))/gi
+const INLINE_ROUTE_QUERY_KEYS = new Set(['key', 'fileId'])
+
+/**
+ * True for the *display-layer* inline route `resolveImageSrc` (see `use-file-content-source.tsx`)
+ * rewrites an embed to — workspace-scoped `/api/workspaces/{workspaceId}/files/inline?key=…`/`?fileId=…`
+ * or public-share-scoped `/api/files/public/{token}/inline?key=…`/`?fileId=…`. This is the shape
+ * actually rendered into `<img src>`, and so what a same-page copy's `text/html` clipboard payload
+ * actually contains — NOT the raw stored reference `extractEmbeddedFileRef` (in
+ * `@/lib/uploads/utils/embedded-image-ref`) recognizes, which only matches the persisted `src` before
+ * that rewrite. Checked separately from (rather than folded into) `extractEmbeddedFileRef` since that
+ * helper is shared with server-side authorization/export code operating on persisted content, where
+ * this display-only shape should never legitimately appear.
+ */
+export function isInlineRouteSrc(src: string): boolean {
+  try {
+    const parsed = new URL(src, 'http://placeholder')
+    if (parsed.origin !== 'http://placeholder') return false
+    if (!parsed.pathname.endsWith('/inline')) return false
+    for (const key of parsed.searchParams.keys()) {
+      if (INLINE_ROUTE_QUERY_KEYS.has(key)) return true
+    }
+    return false
+  } catch {
+    return false
+  }
+}
+
+/**
+ * Extracts every `<img>` `src` value found in `html`, in document order (may contain duplicates).
+ */
+export function extractImgSrcs(html: string): string[] {
+  const srcs: string[] = []
+  for (const match of html.matchAll(IMG_SRC_RE)) {
+    const src = match[1] ?? match[2] ?? match[3]
+    if (src) srcs.push(src)
+  }
+  return srcs
+}
+
+/**
+ * True when `html` contains an `<img>` whose `src` is already one of our own hosted workspace file
+ * references. Copying a rendered `<img>` that's already on the page (e.g. Cmd+C after clicking it to
+ * select it) makes the browser put BOTH `text/html` (the real serialized node, with its real hosted
+ * `src`) AND a synthesized image `File` onto the clipboard — the same "drag a web image out" behavior
+ * that {@link extractImageFiles} alone can't tell apart from a genuinely new external image paste.
+ */
+export function hasHostedImageHtml(html: string, isHostedRef: (src: string) => boolean): boolean {
+  return extractImgSrcs(html).some((src) => isHostedRef(src) || isInlineRouteSrc(src))
+}
+
+/**
+ * True when a paste or drop should be diverted away from the upload-from-file path — it carries
+ * exactly one image file, and the accompanying `text/html` shows it's a same-page copy of an
+ * already-hosted image (see {@link hasHostedImageHtml}) rather than a genuinely new external image.
+ * Content-based (not `view.dragging`-based, for the drop case): `view.dragging` can go briefly stale
+ * (cleared up to ~50ms late by ProseMirror's own `dragend` handler when a prior internal drag was
+ * dropped outside this view) and must never suppress upload of an unrelated, genuinely new file that
+ * happens to land in that window — this check only reacts to what THIS specific event's `html`
+ * actually contains. Gated on exactly one file — a genuinely mixed paste/drop (the hosted image plus a
+ * separate new one) must still upload the new file, not have the whole paste/drop diverted.
+ */
+export function shouldSkipFileUpload(
+  images: File[],
+  html: string,
+  isHostedRef: (src: string) => boolean
+): boolean {
+  return images.length === 1 && Boolean(html) && hasHostedImageHtml(html, isHostedRef)
+}
+
+/** Minimal shape of a ProseMirror image node — just enough to read its type name and attrs. */
+interface ImageLikeNode {
+  type: { name: string }
+  attrs: Record<string, unknown>
+}
+
+/** Minimal shape of a ProseMirror doc — just enough to walk its nodes. */
+interface DescendantsDoc {
+  descendants: (callback: (node: ImageLikeNode) => boolean | undefined) => void
+}
+
+/**
+ * Finds the first `image` node already in `doc` whose *rendered* src (`resolveImageSrc(node.attrs.src)`)
+ * matches one of `targetSrcs`, and returns its attrs — a defensive copy, safe to hand straight to
+ * `insertContentAt`. Returns `null` if no match is found (e.g. the source node was deleted, or this is
+ * genuinely a different document than the one the html was copied from).
+ *
+ * Used to clone a same-page copy/drag of an already-hosted image faithfully — the exact persisted
+ * `src` (and every other attribute: width, height, href, title…) — rather than re-deriving a node from
+ * the clipboard/dataTransfer `html`, whose `src` is `resolveImageSrc`'s rewritten *display* URL, not the
+ * real persisted one. Inserting a node built from that display URL would bake it into the document,
+ * which public share/export/referenced-by-doc tracking don't recognize (they only match the persisted
+ * shape) — this lookup avoids ever constructing such a node in the first place.
+ */
+export function findHostedImageAttrs(
+  doc: DescendantsDoc,
+  targetSrcs: string[],
+  resolveImageSrc: (src: string | undefined) => string | undefined
+): Record<string, unknown> | null {
+  const targets = new Set(targetSrcs)
+  let found: Record<string, unknown> | null = null
+  doc.descendants((node) => {
+    if (found) return false
+    if (node.type.name === 'image') {
+      const resolved = resolveImageSrc(node.attrs.src as string | undefined)
+      if (resolved && targets.has(resolved)) {
+        found = { ...node.attrs }
+        return false
+      }
+    }
+    return true
+  })
+  return found
+}
diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/link-mark-precedence.test.ts b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/link-mark-precedence.test.ts
new file mode 100644
index 00000000000..a2edbbae3e5
--- /dev/null
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/link-mark-precedence.test.ts
@@ -0,0 +1,217 @@
+/**
+ * @vitest-environment jsdom
+ *
+ * A mark stacked on top of another color-setting context must not steal that context's color: an
+ * element's own explicit `color` rule always wins over an inherited value, regardless of how specific
+ * the ancestor's selector is. Two contexts hit this in practice:
+ *
+ * - A link's blue, stacked with bold/italic/strikethrough/inline-code. `strong`/`em`/`code` no longer
+ *   set their own `color` at all (it was redundant with the prose default anyway, and — like the
+ *   `mark`/highlight rule's own `color: inherit` — the absence of a rule is what lets inheritance
+ *   carry through correctly from ANY ambient context, not just links). `del`/`s` genuinely need their
+ *   own dimmer default, so they keep an explicit `color` plus an override for the link case.
+ * - `h6`'s intentionally dimmer `--text-secondary` (vs. every other heading and the prose default,
+ *   both `--text-primary`), stacked with bold/italic — before strong/em's color was removed, a bold
+ *   run inside an `h6` incorrectly showed the brighter `--text-primary` instead of `h6`'s own tone.
+ *
+ * These load the real, shipped `rich-markdown-editor.css` (not a copy) and assert against
+ * `getComputedStyle` in jsdom. jsdom's CSS engine does not resolve `var(...)` references to actual
+ * color values, but it does correctly resolve the cascade/specificity/inheritance winner and returns
+ * that declaration's authored value verbatim — so asserting the winning value is `var(--brand-secondary)`
+ * (vs. e.g. `var(--text-primary)`) is a precise, real assertion about which CSS rule wins, not a proxy.
+ */
+import { readFileSync } from 'node:fs'
+import path from 'node:path'
+import { afterEach, beforeAll, describe, expect, it } from 'vitest'
+
+const CSS_PATH = path.join(__dirname, 'rich-markdown-editor.css')
+const LINK_COLOR = 'var(--brand-secondary)'
+
+beforeAll(() => {
+  const style = document.createElement('style')
+  style.textContent = readFileSync(CSS_PATH, 'utf-8')
+  document.head.appendChild(style)
+})
+
+let container: HTMLDivElement | null = null
+
+afterEach(() => {
+  container?.remove()
+  container = null
+})
+
+/** Mounts `html` inside a `.rich-markdown-prose` container (the real editor's root class) and returns it. */
+function mount(html: string): HTMLDivElement {
+  container = document.createElement('div')
+  container.className = 'rich-markdown-prose'
+  container.innerHTML = html
+  document.body.appendChild(container)
+  return container
+}
+
+function colorOf(el: Element | null): string {
+  if (!el) throw new Error('element not found')
+  return getComputedStyle(el).color
+}
+
+describe('link color baseline (no stacked mark)', () => {
+  it('a plain link is brand-secondary colored', () => {
+    const root = mount('<a href="#">link</a>')
+    expect(colorOf(root.querySelector('a'))).toBe(LINK_COLOR)
+  })
+})
+
+describe('a mark with no link keeps its own color (regression guard: the fix must not force every mark blue)', () => {
+  it.each([
+    { tag: 'strong', html: '<strong>bold</strong>', color: 'var(--text-primary)' },
+    { tag: 'em', html: '<em>italic</em>', color: 'var(--text-primary)' },
+    { tag: 'del', html: '<del>struck</del>', color: 'var(--text-tertiary)' },
+    { tag: 's', html: '<s>struck</s>', color: 'var(--text-tertiary)' },
+    { tag: 'code', html: '<code>code</code>', color: 'var(--text-primary)' },
+  ])('$tag alone renders $color, not link color', ({ tag, html, color }) => {
+    const root = mount(html)
+    expect(colorOf(root.querySelector(tag))).toBe(color)
+    expect(colorOf(root.querySelector(tag))).not.toBe(LINK_COLOR)
+  })
+})
+
+describe('mark nested INSIDE a link (`<a><mark>text</mark></a>`) — link color wins', () => {
+  it.each([
+    { tag: 'strong', html: '<a href="#"><strong>bold link</strong></a>' },
+    { tag: 'em', html: '<a href="#"><em>italic link</em></a>' },
+    { tag: 'del', html: '<a href="#"><del>struck link</del></a>' },
+    { tag: 's', html: '<a href="#"><s>struck link</s></a>' },
+    { tag: 'code', html: '<a href="#"><code>code link</code></a>' },
+  ])('$tag inside a link is link-colored, not its own default color', ({ tag, html }) => {
+    const root = mount(html)
+    expect(colorOf(root.querySelector(tag))).toBe(LINK_COLOR)
+  })
+})
+
+describe('mark WRAPPING a link (`<mark><a>text</a></mark>`) — link color still wins', () => {
+  it.each([
+    { tag: 'strong', html: '<strong><a href="#">bold link</a></strong>' },
+    { tag: 'em', html: '<em><a href="#">italic link</a></em>' },
+    { tag: 'del', html: '<del><a href="#">struck link</a></del>' },
+    { tag: 's', html: '<s><a href="#">struck link</a></s>' },
+    { tag: 'code', html: '<code><a href="#">code link</a></code>' },
+  ])('a link inside $tag is link-colored regardless of nesting direction', ({ tag, html }) => {
+    const root = mount(html)
+    expect(colorOf(root.querySelector('a'))).toBe(LINK_COLOR)
+  })
+})
+
+describe('each mark keeps its own non-color styling even when link-colored', () => {
+  it('bold link keeps font-weight 600', () => {
+    const root = mount('<a href="#"><strong>bold link</strong></a>')
+    const strong = root.querySelector('strong') as HTMLElement
+    expect(colorOf(strong)).toBe(LINK_COLOR)
+    expect(getComputedStyle(strong).fontWeight).toBe('600')
+  })
+
+  it('italic link keeps font-style italic', () => {
+    const root = mount('<a href="#"><em>italic link</em></a>')
+    const em = root.querySelector('em') as HTMLElement
+    expect(colorOf(em)).toBe(LINK_COLOR)
+    expect(getComputedStyle(em).fontStyle).toBe('italic')
+  })
+
+  it('strikethrough link keeps text-decoration line-through (del and s)', () => {
+    for (const tag of ['del', 's']) {
+      const root = mount(`<a href="#"><${tag}>struck link</${tag}></a>`)
+      const el = root.querySelector(tag) as HTMLElement
+      expect(colorOf(el)).toBe(LINK_COLOR)
+      expect(getComputedStyle(el).textDecoration).toContain('line-through')
+      container?.remove()
+    }
+  })
+
+  it('inline-code link keeps its monospace font and background', () => {
+    const root = mount('<a href="#"><code>code link</code></a>')
+    const code = root.querySelector('code') as HTMLElement
+    const computed = getComputedStyle(code)
+    expect(colorOf(code)).toBe(LINK_COLOR)
+    expect(computed.fontFamily).toContain('mono')
+    expect(computed.background).toContain('var(--surface-5)')
+  })
+})
+
+describe('multiple marks stacked together with a link', () => {
+  it('bold + italic + link: link color wins, both font-weight and font-style are preserved', () => {
+    const root = mount('<a href="#"><strong><em>bold italic link</em></strong></a>')
+    const em = root.querySelector('em') as HTMLElement
+    const strong = root.querySelector('strong') as HTMLElement
+    expect(colorOf(em)).toBe(LINK_COLOR)
+    expect(colorOf(strong)).toBe(LINK_COLOR)
+    expect(getComputedStyle(em).fontStyle).toBe('italic')
+    expect(getComputedStyle(strong).fontWeight).toBe('600')
+  })
+
+  it('bold + italic + strikethrough + link: link color wins at every nesting level', () => {
+    const root = mount(
+      '<a href="#"><strong><em><del>bold italic struck link</del></em></strong></a>'
+    )
+    for (const tag of ['strong', 'em', 'del']) {
+      expect(colorOf(root.querySelector(tag))).toBe(LINK_COLOR)
+    }
+  })
+
+  it('a mark stack with NO link present is unaffected by the link-precedence rule', () => {
+    const root = mount('<strong><em>bold italic, no link</em></strong>')
+    expect(colorOf(root.querySelector('em'))).toBe('var(--text-primary)')
+    expect(colorOf(root.querySelector('strong'))).toBe('var(--text-primary)')
+  })
+})
+
+describe('a link elsewhere in the document does not bleed color into unrelated marks', () => {
+  it('a sibling bold run outside any link keeps its own color', () => {
+    const root = mount('<p><a href="#">a link</a> and <strong>bold text</strong></p>')
+    expect(colorOf(root.querySelector('a'))).toBe(LINK_COLOR)
+    expect(colorOf(root.querySelector('strong'))).toBe('var(--text-primary)')
+  })
+})
+
+describe('headings stack correctly with marks (same bug class, a different ambient color)', () => {
+  it.each(['h1', 'h2', 'h3', 'h4', 'h5'])(
+    '%s carries --text-primary, same as bold/italic inside it — no visible regression either way',
+    (tag) => {
+      const root = mount(`<${tag}><strong>bold</strong> <em>italic</em></${tag}>`)
+      expect(colorOf(root.querySelector(tag))).toBe('var(--text-primary)')
+      expect(colorOf(root.querySelector('strong'))).toBe('var(--text-primary)')
+      expect(colorOf(root.querySelector('em'))).toBe('var(--text-primary)')
+    }
+  )
+
+  // h6 is the one heading with its own dimmer tone (--text-secondary, not --text-primary like every
+  // other heading and the prose default) — the exact shape of ambient color strong/em must inherit
+  // rather than reset, the same failure mode as the link case above just triggered by a heading
+  // instead of an <a>.
+  it('h6 keeps its dimmer --text-secondary, and bold/italic inside it inherit that tone (not --text-primary)', () => {
+    const root = mount('<h6><strong>bold</strong> <em>italic</em> plain</h6>')
+    const h6 = root.querySelector('h6') as HTMLElement
+    expect(colorOf(h6)).toBe('var(--text-secondary)')
+    expect(colorOf(root.querySelector('strong'))).toBe('var(--text-secondary)')
+    expect(colorOf(root.querySelector('em'))).toBe('var(--text-secondary)')
+  })
+
+  it('inline code inside h6 also inherits --text-secondary, not its own hardcoded default', () => {
+    const root = mount('<h6><code>code</code></h6>')
+    expect(colorOf(root.querySelector('code'))).toBe('var(--text-secondary)')
+  })
+
+  it('a struck-through run inside h6 keeps its own dimmer tertiary tone (mark-own-color still wins over a non-link ambient context)', () => {
+    const root = mount('<h6><del>struck</del></h6>')
+    expect(colorOf(root.querySelector('del'))).toBe('var(--text-tertiary)')
+  })
+
+  it('an anchor heading (link wrapping the whole heading) still shows link color, unaffected by h6', () => {
+    const root = mount('<h6><a href="#">linked heading</a></h6>')
+    expect(colorOf(root.querySelector('a'))).toBe(LINK_COLOR)
+  })
+
+  it('bold + italic + link inside h6: link color wins over both the mark defaults and h6 itself', () => {
+    const root = mount('<h6><a href="#"><strong><em>bold italic link</em></strong></a></h6>')
+    expect(colorOf(root.querySelector('em'))).toBe(LINK_COLOR)
+    expect(colorOf(root.querySelector('strong'))).toBe(LINK_COLOR)
+  })
+})
diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/rich-markdown-editor.css b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/rich-markdown-editor.css
index c8b56385b56..5c698d25835 100644
--- a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/rich-markdown-editor.css
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/rich-markdown-editor.css
@@ -94,16 +94,23 @@
   color: var(--text-secondary);
 }
 
+/* No explicit `color` on strong/em — an inherited value never beats an element's own explicit rule
+ * regardless of the ancestor selector's specificity, so a hardcoded color here would silently win
+ * over ANY ambient color a ancestor sets that differs from the prose default (a link's blue, `h6`'s
+ * dimmer `--text-secondary`, or any future colored container) — the same failure mode `color:
+ * inherit` on the `mark` (highlight) rule below already avoids. Bold/italic text is meant to carry
+ * the surrounding color, not reset it; omitting `color` here lets normal CSS inheritance do that
+ * correctly in every context, including ones this file doesn't know about yet. */
 .rich-markdown-prose strong {
   font-weight: 600;
-  color: var(--text-primary);
 }
 
 .rich-markdown-prose em {
   font-style: italic;
-  color: var(--text-primary);
 }
 
+/* del/s DO need their own explicit dimmer color (distinct from the surrounding text) as their
+ * default — but see the link-color override below for why that must still yield inside a link. */
 .rich-markdown-prose del,
 .rich-markdown-prose s {
   color: var(--text-tertiary);
@@ -223,15 +230,31 @@
   font-style: italic;
 }
 
+/* No explicit `color` — see the strong/em comment above; inline code composites its own font/
+ * background/radius over whatever color the surrounding context (link, heading, prose default)
+ * already supplies. */
 .rich-markdown-prose code {
   font-family: var(--font-martian-mono, ui-monospace, monospace);
   font-size: 0.875em;
   background: var(--surface-5);
-  color: var(--text-primary);
   border-radius: 4px;
   padding: 0.125rem 0.375rem;
 }
 
+/* del/s are the one mark that both needs its own explicit default color (dimmer than the prose
+ * default, unlike strong/em/code above) AND must still yield it to a link's blue — an inherited
+ * value never beats an element's own explicit rule regardless of the ancestor selector's
+ * specificity, so without this override a struck-through link would show the dimmer tertiary color
+ * instead of the link's blue. Covers both DOM nesting orders since ProseMirror's mark array — and so
+ * the render order marks nest in — depends on which was toggled first, not a fixed schema order.
+ * Declared after the del/s rule above so it wins on source order too, not just specificity. */
+.rich-markdown-prose a del,
+.rich-markdown-prose a s,
+.rich-markdown-prose del a,
+.rich-markdown-prose s a {
+  color: var(--brand-secondary);
+}
+
 .rich-markdown-prose pre,
 .rich-markdown-prose .mermaid-diagram-frame {
   background: var(--surface-5);
diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/rich-markdown-editor.tsx b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/rich-markdown-editor.tsx
index 7114210f8ca..5057c835af9 100644
--- a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/rich-markdown-editor.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/rich-markdown-editor.tsx
@@ -7,13 +7,20 @@ import type { Editor } from '@tiptap/react'
 import { EditorContent, useEditor } from '@tiptap/react'
 import { useRouter } from 'next/navigation'
 import type { WorkspaceFileRecord } from '@/lib/uploads/contexts/workspace'
+import { extractEmbeddedFileRef } from '@/lib/uploads/utils/embedded-image-ref'
 import { useUploadWorkspaceFile } from '@/hooks/queries/workspace-files'
 import type { SaveStatus } from '@/hooks/use-autosave'
+import { useFileContentSource } from '@/hooks/use-file-content-source'
 import { PreviewLoadingFrame } from '../preview-shared'
 import { useEditableFileContent } from '../use-editable-file-content'
 import { createMarkdownEditorExtensions } from './editor-extensions'
 import { findHeadingPos } from './heading-anchors'
-import { extractImageFiles } from './image-paste'
+import {
+  extractImageFiles,
+  extractImgSrcs,
+  findHostedImageAttrs,
+  shouldSkipFileUpload,
+} from './image-paste'
 import {
   applyFrontmatter,
   normalizeLinkHref,
@@ -208,6 +215,7 @@ export function LoadedRichMarkdownEditor({
   const containerRef = useRef<HTMLDivElement>(null)
   const uploadFile = useUploadWorkspaceFile()
   const editorInstanceRef = useRef<Editor | null>(null)
+  const source = useFileContentSource()
 
   /**
    * The `/Image` slash command opens this hidden picker; `pendingImagePosRef` holds the caret position
@@ -250,6 +258,31 @@ export function LoadedRichMarkdownEditor({
     }
   }
 
+  /**
+   * A same-page copy/drag of an already-hosted `<img>` carries the clipboard/dataTransfer `html`'s
+   * *display* src (`source.resolveImageSrc`'s rewrite), not the real persisted one — inserting a node
+   * built straight from that html would bake the display-only URL into the document, breaking public
+   * share/export/referenced-by-doc tracking for it (they only recognize the persisted shape).
+   * `findHostedImageAttrs` finds the real, already-present node with a matching resolved src instead,
+   * so the clone gets the exact real `src` (and every other attribute — width, href, title…) rather
+   * than a re-derived guess. Returns `false` (falls through to a normal upload) if no match is found,
+   * which is always correct, just occasionally a redundant upload — unlike blindly trusting the html.
+   */
+  const cloneHostedImageRef = useRef<(imgSrcs: string[], at: number) => boolean>(() => false)
+  cloneHostedImageRef.current = (imgSrcs, at) => {
+    const editor = editorInstanceRef.current
+    if (!editor) return false
+    const matchedAttrs = findHostedImageAttrs(editor.state.doc, imgSrcs, source.resolveImageSrc)
+    if (!matchedAttrs) return false
+    const safePosition = Math.min(at, editor.state.doc.content.size)
+    try {
+      editor.chain().insertContentAt(safePosition, { type: 'image', attrs: matchedAttrs }).run()
+      return true
+    } catch {
+      return false
+    }
+  }
+
   const editor = useEditor({
     extensions: EXTENSIONS,
     editable: isEditable,
@@ -298,9 +331,32 @@ export function LoadedRichMarkdownEditor({
         window.open(normalized, '_blank', 'noopener,noreferrer')
         return true
       },
+      /**
+       * Inserts pasted image files at the caret. A same-page copy of an already-hosted `<img>` (e.g.
+       * Cmd+C after clicking it to select it) makes the browser add BOTH `text/html` (the real node,
+       * with its real hosted `src`) AND a synthesized image `File` to the clipboard — indistinguishable
+       * from a genuine external image paste by `clipboardData` files/items alone. When the HTML sibling
+       * already names one of our own hosted files, look up the matching node already in this doc and
+       * clone ITS real attrs (see `cloneHostedImageRef`) instead of re-uploading the pasted bytes as a
+       * brand-new, distinct file — letting the editor's DEFAULT html-based paste do that clone instead
+       * would persist the html's display-layer src rather than the real one. Only applied when exactly
+       * one image file is offered: a genuinely mixed paste (the hosted image plus a separate new one)
+       * must still upload the new file rather than have the whole paste diverted by this bypass.
+       */
       handlePaste: (view, event) => {
         if (!view.editable) return false
         const images = extractImageFiles(event.clipboardData)
+        const html = event.clipboardData?.getData('text/html') ?? ''
+        if (shouldSkipFileUpload(images, html, (src) => extractEmbeddedFileRef(src) !== null)) {
+          const cloned = cloneHostedImageRef.current(
+            extractImgSrcs(html),
+            view.state.selection.from
+          )
+          if (cloned) {
+            event.preventDefault()
+            return true
+          }
+        }
         if (images.length === 0) return false
         event.preventDefault()
         void insertImagesRef.current(images, view.state.selection.from)
@@ -310,10 +366,26 @@ export function LoadedRichMarkdownEditor({
        * Inserts dropped image files at the drop point. Any other file drop (e.g. a PDF) is swallowed so
        * the browser doesn't navigate away from the editor; internal text drags carry no files and fall
        * through to the default behavior.
+       *
+       * Dragging an existing image node to reorder it is also an internal drag, but the browser's
+       * native drag-and-drop synthesizes an image `File` into `event.dataTransfer` for a dragged `<img>`
+       * (the same mechanism that lets a user drag a web image out to their desktop) — indistinguishable
+       * from a real external drop by `dataTransfer` files/items alone. When the accompanying `text/html`
+       * shows it's a same-page drag of an already-hosted image, bail out and let ProseMirror's own
+       * default move logic run — it relocates the actual existing node object (`dragging.node`), never
+       * re-parsing html, so (unlike the paste case above) there's no display-vs-persisted src risk here.
+       * Checked from `html`, not `view.dragging`, so a stale `dragging` flag (ProseMirror clears it up
+       * to ~50ms late via `dragend` when a prior internal drag was dropped outside this view) can never
+       * suppress the plain-file swallow guard below for an unrelated drop that happens to land in that
+       * window — this only reacts to what THIS specific drop's `html` actually contains.
        */
       handleDrop: (view, event) => {
         if (!view.editable) return false
         const images = extractImageFiles(event.dataTransfer)
+        const html = event.dataTransfer?.getData('text/html') ?? ''
+        if (shouldSkipFileUpload(images, html, (src) => extractEmbeddedFileRef(src) !== null)) {
+          return false
+        }
         if (images.length > 0) {
           event.preventDefault()
           const dropPos = view.posAtCoords({ left: event.clientX, top: event.clientY })?.pos