diff --git a/docs/resources/changelog.md b/docs/resources/changelog.md
index bf30d5bcf..b6016257e 100644
--- a/docs/resources/changelog.md
+++ b/docs/resources/changelog.md
@@ -10,6 +10,7 @@ _During the beta period, these restrictions may be relaxed in the event of a mis
 
 - CodePen examples will now open in light or dark depending on your current preference
 - Fixed a bug where tag names weren't being generated in `vscode.html-custom-data.json` [#593](https://github.com/shoelace-style/shoelace/pull/593)
+- Fixed a bug in `<sl-tooltip>` where the tooltip wouldn't reposition when content changed
 - Upgraded the status of `<sl-qr-code>` from experimental to stable
 
 ## 2.0.0-beta.61
diff --git a/src/components/tooltip/tooltip.ts b/src/components/tooltip/tooltip.ts
index fcebb9c48..8b952d622 100644
--- a/src/components/tooltip/tooltip.ts
+++ b/src/components/tooltip/tooltip.ts
@@ -269,6 +269,13 @@ export default class SlTooltip extends LitElement {
     this.syncOptions();
   }
 
+  @watch('content')
+  handleContentChange() {
+    if (this.popover && this.open) {
+      this.popover.update();
+    }
+  }
+
   @watch('disabled')
   handleDisabledChange() {
     if (this.disabled && this.open) {
@@ -331,7 +338,7 @@ export default class SlTooltip extends LitElement {
           role="tooltip"
           aria-hidden=${this.open ? 'false' : 'true'}
         >
-          <slot name="content">${this.content}</slot>
+          <slot name="content" @slotchange=${this.handleContentChange}> ${this.content} </slot>
         </div>
       </div>
     `;