diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3fa10e00e..930d43624 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -86,6 +86,7 @@
 - Bugfix: Reply contexts now use the color of the replied-to message. (#5145)
 - Bugfix: Fixed top-level window getting stuck after opening settings. (#5161, #5166)
 - Bugfix: Fixed link info not updating without moving the cursor. (#5178)
+- Bugfix: Fixed tooltips getting out of bounds when loading images. (#5186)
 - Dev: Run miniaudio in a separate thread, and simplify it to not manage the device ourselves. There's a chance the simplification is a bad idea. (#4978)
 - Dev: Change clang-format from v14 to v16. (#4929)
 - Dev: Fixed UTF16 encoding of `modes` file for the installer. (#4791)
diff --git a/src/widgets/BaseWindow.cpp b/src/widgets/BaseWindow.cpp
index ca7d02d44..c34edf96f 100644
--- a/src/widgets/BaseWindow.cpp
+++ b/src/widgets/BaseWindow.cpp
@@ -531,14 +531,29 @@ void BaseWindow::leaveEvent(QEvent *)
 
 void BaseWindow::moveTo(QPoint point, widgets::BoundsChecking mode)
 {
+    this->lastBoundsCheckPosition_ = point;
+    this->lastBoundsCheckMode_ = mode;
     widgets::moveWindowTo(this, point, mode);
 }
 
 void BaseWindow::showAndMoveTo(QPoint point, widgets::BoundsChecking mode)
 {
+    this->lastBoundsCheckPosition_ = point;
+    this->lastBoundsCheckMode_ = mode;
     widgets::showAndMoveWindowTo(this, point, mode);
 }
 
+bool BaseWindow::applyLastBoundsCheck()
+{
+    if (this->lastBoundsCheckMode_ == widgets::BoundsChecking::Off)
+    {
+        return false;
+    }
+
+    this->moveTo(this->lastBoundsCheckPosition_, this->lastBoundsCheckMode_);
+    return true;
+}
+
 void BaseWindow::resizeEvent(QResizeEvent *)
 {
     // Queue up save because: Window resized
diff --git a/src/widgets/BaseWindow.hpp b/src/widgets/BaseWindow.hpp
index fa7526b49..e59c8ae81 100644
--- a/src/widgets/BaseWindow.hpp
+++ b/src/widgets/BaseWindow.hpp
@@ -65,6 +65,15 @@ public:
      **/
     void showAndMoveTo(QPoint point, widgets::BoundsChecking mode);
 
+    /// @brief Applies the last moveTo operation if that one was bounds-checked
+    ///
+    /// If there was a previous moveTo or showAndMoveTo operation with a mode
+    /// other than `Off`, a moveTo is repeated with the last supplied @a point
+    /// and @a mode. Note that in the case of showAndMoveTo, moveTo is run.
+    ///
+    /// @returns true if there was a previous bounds-checked moveTo operation
+    bool applyLastBoundsCheck();
+
     float scale() const override;
     float qtFontScale() const;
 
@@ -152,6 +161,11 @@ private:
         std::vector<Button *> buttons;
     } ui_;
 
+    /// The last @a pos from moveTo and showAndMoveTo
+    QPoint lastBoundsCheckPosition_;
+    /// The last @a mode from moveTo and showAndMoveTo
+    widgets::BoundsChecking lastBoundsCheckMode_ = widgets::BoundsChecking::Off;
+
 #ifdef USEWINSDK
     /// @brief Returns the HWND of this window if it has one
     ///
diff --git a/src/widgets/TooltipWidget.cpp b/src/widgets/TooltipWidget.cpp
index b40931e5c..2e1ddf89e 100644
--- a/src/widgets/TooltipWidget.cpp
+++ b/src/widgets/TooltipWidget.cpp
@@ -90,6 +90,7 @@ TooltipWidget::TooltipWidget(BaseWidget *parent)
             if (needSizeAdjustment)
             {
                 this->adjustSize();
+                this->applyLastBoundsCheck();
             }
         });
 }
diff --git a/src/widgets/helper/ChannelView.cpp b/src/widgets/helper/ChannelView.cpp
index fe779174a..a66059bb8 100644
--- a/src/widgets/helper/ChannelView.cpp
+++ b/src/widgets/helper/ChannelView.cpp
@@ -3121,6 +3121,7 @@ void ChannelView::pendingLinkInfoStateChanged()
         return;
     }
     this->setLinkInfoTooltip(this->pendingLinkInfo_.data());
+    this->tooltipWidget_->applyLastBoundsCheck();
 }
 
 }  // namespace chatterino