diff --git a/packages/webawesome/docs/docs/resources/changelog.md b/packages/webawesome/docs/docs/resources/changelog.md
index 1fbfbe6a5..5549e7659 100644
--- a/packages/webawesome/docs/docs/resources/changelog.md
+++ b/packages/webawesome/docs/docs/resources/changelog.md
@@ -30,10 +30,11 @@ Components with the <wa-badge variant="warning">Experimental</wa-badge> badge sh
 - Fixed a bug in `<wa-checkbox>` where its value would revert to `""` when checked / unchecked [pr:1547]
 - Fixed a bug that caused icon button labels to not render in frameworks [issue:1542]
 - Fixed a bug in `<wa-details>` that caused the `name` property not to reflect [pr:1538]
-- Modified `<wa-slider>` to only show the tooltip on the handle being dragged when in range mode [issue:1320]
 - Fixed a bug in `<wa-dialog>` and `<wa-drawer>` that prevented focus from being set on the dialog/drawer when opened [issue:1302]
 - Fixed an overflow style that was causing tab group content to be unnecessarily truncated [issue:1401]
 - Fixed a bug in `<wa-icon>` that caused icon buttons to render when non-text nodes were slotted in [issue:1475]
+- Fixed a bug in `<wa-tooltip>` that prevented tooltips from showing when disconnecting and then reconnecting to the DOM [issue:1595]
+- Modified `<wa-slider>` to only show the tooltip on the handle being dragged when in range mode [issue:1320]
 
 ## 3.0.0-beta.6
 
@@ -477,4 +478,4 @@ Many of these changes and improvements were the direct result of feedback from u
 
 </details>
 
-Did we miss something? [Let us know!](https://github.com/shoelace-style/webawesome/discussions)
\ No newline at end of file
+Did we miss something? [Let us know!](https://github.com/shoelace-style/webawesome/discussions)
diff --git a/packages/webawesome/src/components/tooltip/tooltip.ts b/packages/webawesome/src/components/tooltip/tooltip.ts
index e4c103d94..9c16798c5 100644
--- a/packages/webawesome/src/components/tooltip/tooltip.ts
+++ b/packages/webawesome/src/components/tooltip/tooltip.ts
@@ -101,6 +101,11 @@ export default class WaTooltip extends WebAwesomeElement {
   connectedCallback() {
     super.connectedCallback();
 
+    // Recreate event controller if it was aborted
+    if (this.eventController.signal.aborted) {
+      this.eventController = new AbortController();
+    }
+
     // TODO: This is a hack that I need to revisit [Konnor]
     if (this.open) {
       this.open = false;
@@ -113,6 +118,15 @@ export default class WaTooltip extends WebAwesomeElement {
     if (!this.id) {
       this.id = uniqueId('wa-tooltip-');
     }
+
+    // Re-establish anchor connection after being disconnected
+    if (this.for && this.anchor) {
+      this.anchor = null; // force reattach
+      this.handleForChange();
+    } else if (this.for) {
+      // Initial connection
+      this.handleForChange();
+    }
   }
 
   disconnectedCallback() {