diff --git a/internal/markdown/markdown.go b/internal/markdown/markdown.go
index 4d107469f..f6636309a 100644
--- a/internal/markdown/markdown.go
+++ b/internal/markdown/markdown.go
@@ -119,6 +119,26 @@ func (s *service) parse(content []byte) (gast.Node, error) {
 	return doc, nil
 }
 
+func isTagNodeInLinkOrImage(n gast.Node) bool {
+	for parent := n.Parent(); parent != nil; parent = parent.Parent() {
+		switch parent.Kind() {
+		case gast.KindLink, gast.KindImage:
+			return true
+		default:
+			// Keep walking ancestors.
+		}
+	}
+	return false
+}
+
+func asMemoTagNode(n gast.Node) (*mast.TagNode, bool) {
+	tagNode, ok := n.(*mast.TagNode)
+	if !ok || isTagNodeInLinkOrImage(n) {
+		return nil, false
+	}
+	return tagNode, true
+}
+
 // ExtractTags returns all #tags found in content.
 func (s *service) ExtractTags(content []byte) ([]string, error) {
 	root, err := s.parse(content)
@@ -134,8 +154,7 @@ func (s *service) ExtractTags(content []byte) ([]string, error) {
 			return gast.WalkContinue, nil
 		}
 
-		// Check for custom TagNode
-		if tagNode, ok := n.(*mast.TagNode); ok {
+		if tagNode, ok := asMemoTagNode(n); ok {
 			tags = append(tags, string(tagNode.Tag))
 		}
 
@@ -354,8 +373,7 @@ func (s *service) ExtractAll(content []byte) (*ExtractedData, error) {
 			return gast.WalkContinue, nil
 		}
 
-		// Extract tags
-		if tagNode, ok := n.(*mast.TagNode); ok {
+		if tagNode, ok := asMemoTagNode(n); ok {
 			data.Tags = append(data.Tags, string(tagNode.Tag))
 		}
 		if mentionNode, ok := n.(*mast.MentionNode); ok {
@@ -416,8 +434,7 @@ func (s *service) RenameTag(content []byte, oldTag, newTag string) (string, erro
 			return gast.WalkContinue, nil
 		}
 
-		// Check for custom TagNode and rename if it matches
-		if tagNode, ok := n.(*mast.TagNode); ok {
+		if tagNode, ok := asMemoTagNode(n); ok {
 			if string(tagNode.Tag) == oldTag {
 				tagNode.Tag = []byte(newTag)
 			}
diff --git a/internal/markdown/markdown_test.go b/internal/markdown/markdown_test.go
index 3e6a1fc86..6ac1778ff 100644
--- a/internal/markdown/markdown_test.go
+++ b/internal/markdown/markdown_test.go
@@ -349,6 +349,20 @@ func TestExtractAllMentions(t *testing.T) {
 	assert.ElementsMatch(t, []string{"tag"}, data.Tags)
 }
 
+func TestExtractAllSkipsTagsInsideLinks(t *testing.T) {
+	svc := NewService(WithTagExtension())
+
+	data, err := svc.ExtractAll([]byte(
+		"[release #notes](https://example.com/releases#release-notes)\n\n" +
+			"![preview #image](https://example.com/image#preview)\n\n" +
+			"Outside #memo-tag",
+	))
+	require.NoError(t, err)
+
+	assert.ElementsMatch(t, []string{"memo-tag"}, data.Tags)
+	assert.True(t, data.Property.HasLink)
+}
+
 func TestExtractTags(t *testing.T) {
 	tests := []struct {
 		name     string
@@ -410,6 +424,30 @@ func TestExtractTags(t *testing.T) {
 			withExt:  true,
 			expected: []string{"todo", "done"},
 		},
+		{
+			name:     "autolink URL fragment not tag",
+			content:  "https://github.com/dmtrKovalenko/fff#pi-agent-extension\n\nProject #memo-tag",
+			withExt:  true,
+			expected: []string{"memo-tag"},
+		},
+		{
+			name:     "markdown link text and fragment not tags",
+			content:  "[release #notes](https://example.com/releases#release-notes) Outside #memo-tag",
+			withExt:  true,
+			expected: []string{"memo-tag"},
+		},
+		{
+			name:     "reference link text and fragment not tags",
+			content:  "[reference #anchor][docs]\n\n[docs]: https://example.com/docs#reference-anchor\n\nOutside #memo-tag",
+			withExt:  true,
+			expected: []string{"memo-tag"},
+		},
+		{
+			name:     "image alt text and fragment not tags",
+			content:  "![preview #image](https://example.com/image#preview)\n\nOutside #memo-tag",
+			withExt:  true,
+			expected: []string{"memo-tag"},
+		},
 		{
 			name:     "no extension enabled",
 			content:  "Text with #tag",
@@ -470,6 +508,19 @@ func TestExtractTags(t *testing.T) {
 	}
 }
 
+func TestRenameTagSkipsTagsInsideLinks(t *testing.T) {
+	svc := NewService(WithTagExtension())
+
+	result, err := svc.RenameTag(
+		[]byte("[release #notes](https://example.com/releases#release-notes)\n\nOutside #notes"),
+		"notes",
+		"done",
+	)
+	require.NoError(t, err)
+
+	assert.Equal(t, "[release #notes](https://example.com/releases#release-notes)\n\nOutside #done", result)
+}
+
 func TestUniquePreserveCase(t *testing.T) {
 	tests := []struct {
 		name     string
diff --git a/web/src/utils/remark-plugins/remark-tag.ts b/web/src/utils/remark-plugins/remark-tag.ts
index 24a0efbcb..96f11408e 100644
--- a/web/src/utils/remark-plugins/remark-tag.ts
+++ b/web/src/utils/remark-plugins/remark-tag.ts
@@ -1,6 +1,5 @@
 import type { Root, Text } from "mdast";
 import type { Node as UnistNode } from "unist";
-import { visit } from "unist-util-visit";
 import type { TagNode, TagNodeData } from "@/types/markdown";
 
 const MAX_TAG_LENGTH = 100;
@@ -81,17 +80,27 @@ function createTagNode(tagValue: string): TagNode {
   } as TagNode;
 }
 
-export const remarkTag = () => {
-  return (tree: Root) => {
-    visit(tree, (node, index, parent) => {
-      if (node.type !== "text" || !parent || index === null) return;
+type ParentNode = UnistNode & { children: UnistNode[] };
 
-      const textNode = node as Text;
-      const text = textNode.value;
-      const segments = parseTagsFromText(text);
+function isParentNode(node: UnistNode): node is ParentNode {
+  return Array.isArray((node as { children?: unknown }).children);
+}
+
+function isLinkNode(node: UnistNode): boolean {
+  return node.type === "link" || node.type === "linkReference";
+}
+
+function transformTagTextNodes(parent: ParentNode, insideLink: boolean): void {
+  for (let index = 0; index < parent.children.length; index++) {
+    const child = parent.children[index];
+    const childInsideLink = insideLink || isLinkNode(child);
+
+    if (child.type === "text" && !childInsideLink) {
+      const textNode = child as Text;
+      const segments = parseTagsFromText(textNode.value);
 
       if (segments.every((seg) => seg.type === "text")) {
-        return;
+        continue;
       }
 
       const newNodes = segments.map((segment) => {
@@ -104,9 +113,19 @@ export const remarkTag = () => {
         } as Text;
       });
 
-      if (typeof index === "number" && parent) {
-        (parent.children as UnistNode[]).splice(index, 1, ...(newNodes as UnistNode[]));
-      }
-    });
+      parent.children.splice(index, 1, ...(newNodes as UnistNode[]));
+      index += newNodes.length - 1;
+      continue;
+    }
+
+    if (isParentNode(child)) {
+      transformTagTextNodes(child, childInsideLink);
+    }
+  }
+}
+
+export const remarkTag = () => {
+  return (tree: Root) => {
+    transformTagTextNodes(tree as ParentNode, false);
   };
 };
diff --git a/web/tests/remark-tag.test.tsx b/web/tests/remark-tag.test.tsx
new file mode 100644
index 000000000..c4d26c90f
--- /dev/null
+++ b/web/tests/remark-tag.test.tsx
@@ -0,0 +1,54 @@
+import { renderToStaticMarkup } from "react-dom/server";
+import ReactMarkdown from "react-markdown";
+import remarkGfm from "remark-gfm";
+import { describe, expect, it } from "vitest";
+import { remarkTag } from "@/utils/remark-plugins/remark-tag";
+
+const renderMarkdown = (content: string): string =>
+  renderToStaticMarkup(
+    <ReactMarkdown remarkPlugins={[remarkGfm, remarkTag]}>
+      {content}
+    </ReactMarkdown>,
+  );
+
+describe("remarkTag", () => {
+  it("does not turn URL fragments inside autolinks into tags", () => {
+    const html = renderMarkdown("https://github.com/dmtrKovalenko/fff#pi-agent-extension\n\nProject #memo-tag");
+
+    expect(html).toContain('href="https://github.com/dmtrKovalenko/fff#pi-agent-extension"');
+    expect(html).not.toContain('data-tag="pi-agent-extension"');
+    expect(html).toContain('data-tag="memo-tag"');
+  });
+
+  it("does not turn link text or reference link fragments into tags", () => {
+    const html = renderMarkdown(
+      [
+        "[release #notes](https://example.com/releases#release-notes)",
+        "[**section #heading**](https://example.com/docs#section-heading)",
+        "![preview #image](https://example.com/image#preview)",
+        "[reference #anchor][docs]",
+        "",
+        "[docs]: https://example.com/docs#reference-anchor",
+        "",
+        "Outside #memo-tag",
+      ].join("\n"),
+    );
+
+    expect(html).not.toContain('data-tag="notes"');
+    expect(html).not.toContain('data-tag="heading"');
+    expect(html).not.toContain('data-tag="image"');
+    expect(html).not.toContain('data-tag="anchor"');
+    expect(html).not.toContain('data-tag="release-notes"');
+    expect(html).not.toContain('data-tag="section-heading"');
+    expect(html).not.toContain('data-tag="preview"');
+    expect(html).not.toContain('data-tag="reference-anchor"');
+    expect(html).toContain('data-tag="memo-tag"');
+  });
+
+  it("continues to turn formatted text outside links into tags", () => {
+    const html = renderMarkdown("**#urgent** and _#later_");
+
+    expect(html).toContain('data-tag="urgent"');
+    expect(html).toContain('data-tag="later"');
+  });
+});