diff --git a/distribution/changelog.txt b/distribution/changelog.txt
index 1e4a86108f..b16037a5f8 100644
--- a/distribution/changelog.txt
+++ b/distribution/changelog.txt
@@ -27,6 +27,7 @@
 - Fix: [#19924] Destructible cheat does not allow partial ride modification.
 - Fix: [#19950] Mine train block brake supports drawn incorrectly.
 - Fix: [#19987] [Plugin] ‘SetCheatAction’ has wrong ID in plugin API.
+- Fix: [#19991] Crash using cut-away view.
 
 0.4.4 (2023-03-28)
 ------------------------------------------------------------------------
diff --git a/src/openrct2/interface/Viewport.cpp b/src/openrct2/interface/Viewport.cpp
index 7b3f98345c..3b257b9545 100644
--- a/src/openrct2/interface/Viewport.cpp
+++ b/src/openrct2/interface/Viewport.cpp
@@ -1834,10 +1834,10 @@ InteractionInfo SetInteractionInfoFromPaintSession(PaintSession* session, uint32
 {
     PROFILED_FUNCTION();
 
-    PaintStruct* ps = &session->PaintHead;
     InteractionInfo info{};
 
-    while ((ps = ps->NextQuadrantEntry) != nullptr)
+    PaintStruct* ps = session->PaintHead;
+    while (ps != nullptr)
     {
         PaintStruct* old_ps = ps;
         PaintStruct* next_ps = ps;
@@ -1868,7 +1868,7 @@ InteractionInfo SetInteractionInfoFromPaintSession(PaintSession* session, uint32
         }
 #pragma GCC diagnostic pop
 
-        ps = old_ps;
+        ps = old_ps->NextQuadrantEntry;
     }
     return info;
 }
diff --git a/src/openrct2/paint/Paint.cpp b/src/openrct2/paint/Paint.cpp
index e2c8519e02..0e2500a0cf 100644
--- a/src/openrct2/paint/Paint.cpp
+++ b/src/openrct2/paint/Paint.cpp
@@ -447,9 +447,9 @@ static PaintStruct* PaintArrangeStructsHelperRotation(PaintStruct* psQuadrantEnt
 // Iterates over all the quadrant lists and links them together as a
 // singly linked list.
 // The paint session has a head member which is the first entry.
-static void PaintStructsLinkQuadrants(PaintSessionCore& session)
+static void PaintStructsLinkQuadrants(PaintSessionCore& session, PaintStruct& psHead)
 {
-    PaintStruct* ps = &session.PaintHead;
+    PaintStruct* ps = &psHead;
     ps->NextQuadrantEntry = nullptr;
 
     uint32_t quadrantIndex = session.QuadrantBackIndex;
@@ -477,15 +477,21 @@ template<int TRotation> static void PaintSessionArrangeImpl(PaintSessionCore& se
         return;
     }
 
-    PaintStructsLinkQuadrants(session);
+    // psHead is an intermediate node that is used to link all the quadrant lists together,
+    // this was previously stored in PaintSession but only the NextQuadrantEntry is relevant here.
+    // The head node is not part of the linked list and just serves as an entry point.
+    PaintStruct psHead{};
+    PaintStructsLinkQuadrants(session, psHead);
 
     PaintStruct* psNextQuadrant = PaintArrangeStructsHelperRotation<TRotation>(
-        &session.PaintHead, session.QuadrantBackIndex, PaintSortFlags::Neighbour);
+        &psHead, session.QuadrantBackIndex, PaintSortFlags::Neighbour);
 
     while (++quadrantIndex < session.QuadrantFrontIndex)
     {
         psNextQuadrant = PaintArrangeStructsHelperRotation<TRotation>(psNextQuadrant, quadrantIndex, PaintSortFlags::None);
     }
+
+    session.PaintHead = psHead.NextQuadrantEntry;
 }
 
 using PaintArrangeWithRotation = void (*)(PaintSessionCore& session);
@@ -552,13 +558,9 @@ void PaintDrawStructs(PaintSession& session)
 {
     PROFILED_FUNCTION();
 
-    PaintStruct* ps = &session.PaintHead;
-
-    for (ps = ps->NextQuadrantEntry; ps != nullptr;)
+    for (PaintStruct* ps = session.PaintHead; ps != nullptr; ps = ps->NextQuadrantEntry)
     {
         PaintDrawStruct(session, ps);
-
-        ps = ps->NextQuadrantEntry;
     }
 }
 
@@ -691,7 +693,7 @@ PaintSession* PaintSessionAlloc(DrawPixelInfo& dpi, uint32_t viewFlags)
     return GetContext()->GetPainter()->CreateSession(dpi, viewFlags);
 }
 
-void PaintSessionFree([[maybe_unused]] PaintSession* session)
+void PaintSessionFree(PaintSession* session)
 {
     GetContext()->GetPainter()->ReleaseSession(session);
 }
diff --git a/src/openrct2/paint/Paint.h b/src/openrct2/paint/Paint.h
index f1b049cac8..53c21fdc9b 100644
--- a/src/openrct2/paint/Paint.h
+++ b/src/openrct2/paint/Paint.h
@@ -179,7 +179,7 @@ public:
 
 struct PaintSessionCore
 {
-    PaintStruct PaintHead;
+    PaintStruct* PaintHead;
     PaintStruct* Quadrants[MaxPaintQuadrants];
     PaintStruct* LastPS;
     PaintStringStruct* PSStringHead;
diff --git a/src/openrct2/paint/Painter.cpp b/src/openrct2/paint/Painter.cpp
index 7d770c5bd1..989aa1591a 100644
--- a/src/openrct2/paint/Painter.cpp
+++ b/src/openrct2/paint/Painter.cpp
@@ -160,6 +160,7 @@ PaintSession* Painter::CreateSession(DrawPixelInfo& dpi, uint32_t viewFlags)
     session->Flags = 0;
 
     std::fill(std::begin(session->Quadrants), std::end(session->Quadrants), nullptr);
+    session->PaintHead = nullptr;
     session->LastPS = nullptr;
     session->LastAttachedPS = nullptr;
     session->PSStringHead = nullptr;