diff --git a/win32ss/gdi/ntgdi/freetype.c b/win32ss/gdi/ntgdi/freetype.c
index 42d797137fd..d901e2532ff 100644
--- a/win32ss/gdi/ntgdi/freetype.c
+++ b/win32ss/gdi/ntgdi/freetype.c
@@ -1781,21 +1781,17 @@ FillTMEx(TEXTMETRICW *TM, PFONTGDI FontGDI,
         return;
     }
 
-    if (pOS2->usWinAscent + pOS2->usWinDescent == 0)
+    if ((FT_Short)pOS2->usWinAscent + (FT_Short)pOS2->usWinDescent == 0)
     {
         Ascent = pHori->Ascender;
         Descent = -pHori->Descender;
     }
     else
     {
-        Ascent = pOS2->usWinAscent;
-        Descent = pOS2->usWinDescent;
+        Ascent = (FT_Short)pOS2->usWinAscent;
+        Descent = (FT_Short)pOS2->usWinDescent;
     }
 
-    if (FontGDI->Magic != FONTGDI_MAGIC)
-    {
-        IntRequestFontSize(NULL, FontGDI, 0, 0);
-    }
     TM->tmAscent = FontGDI->tmAscent;
     TM->tmDescent = FontGDI->tmDescent;
     TM->tmHeight = TM->tmAscent + TM->tmDescent;
@@ -2562,7 +2558,7 @@ FontFamilyFillInfo(PFONTFAMILYINFO Info, LPCWSTR FaceName,
     }
 
     Ntm->ntmSizeEM = Otm->otmEMSquare;
-    Ntm->ntmCellHeight = pOS2->usWinAscent + pOS2->usWinDescent;
+    Ntm->ntmCellHeight = (FT_Short)pOS2->usWinAscent + (FT_Short)pOS2->usWinDescent;
     Ntm->ntmAvgWidth = 0;
 
     ExFreePoolWithTag(Otm, GDITAG_TEXT);
@@ -3217,12 +3213,20 @@ IntRequestFontSize(PDC dc, PFONTGDI FontGDI, LONG lfWidth, LONG lfHeight)
         return FT_Request_Size(face, &req);
     }
 
-    /* See also: https://docs.microsoft.com/en-us/typography/opentype/spec/os2#fsselection */
+    /*
+     * NOTE: We cast TT_OS2.usWinAscent and TT_OS2.usWinDescent to signed FT_Short.
+     * Why? See: https://docs.microsoft.com/en-us/typography/opentype/spec/os2#uswindescent
+     *
+     * > usWinDescent is "usually" a positive value ...
+     *
+     * We can read it as "not always". See CORE-14994.
+     * See also: https://docs.microsoft.com/en-us/typography/opentype/spec/os2#fsselection
+     */
 #define FM_SEL_USE_TYPO_METRICS 0x80
     if (lfHeight > 0)
     {
         /* case (A): lfHeight is positive */
-        Sum = pOS2->usWinAscent + pOS2->usWinDescent;
+        Sum = (FT_Short)pOS2->usWinAscent + (FT_Short)pOS2->usWinDescent;
         if (Sum == 0 || (pOS2->fsSelection & FM_SEL_USE_TYPO_METRICS))
         {
             Ascent = pHori->Ascender;
@@ -3231,8 +3235,8 @@ IntRequestFontSize(PDC dc, PFONTGDI FontGDI, LONG lfWidth, LONG lfHeight)
         }
         else
         {
-            Ascent = pOS2->usWinAscent;
-            Descent = pOS2->usWinDescent;
+            Ascent = (FT_Short)pOS2->usWinAscent;
+            Descent = (FT_Short)pOS2->usWinDescent;
         }
 
         FontGDI->tmAscent = FT_MulDiv(lfHeight, Ascent, Sum);
@@ -3250,8 +3254,8 @@ IntRequestFontSize(PDC dc, PFONTGDI FontGDI, LONG lfWidth, LONG lfHeight)
         }
         else
         {
-            FontGDI->tmAscent = FT_MulDiv(-lfHeight, pOS2->usWinAscent, face->units_per_EM);
-            FontGDI->tmDescent = FT_MulDiv(-lfHeight, pOS2->usWinDescent, face->units_per_EM);
+            FontGDI->tmAscent = FT_MulDiv(-lfHeight, (FT_Short)pOS2->usWinAscent, face->units_per_EM);
+            FontGDI->tmDescent = FT_MulDiv(-lfHeight, (FT_Short)pOS2->usWinDescent, face->units_per_EM);
         }
         FontGDI->tmHeight = FontGDI->tmAscent + FontGDI->tmDescent;
         FontGDI->tmInternalLeading = FontGDI->tmHeight + lfHeight;
@@ -3263,10 +3267,7 @@ IntRequestFontSize(PDC dc, PFONTGDI FontGDI, LONG lfWidth, LONG lfHeight)
     FontGDI->EmHeight = min(FontGDI->EmHeight, USHORT_MAX);
     FontGDI->Magic = FONTGDI_MAGIC;
 
-    if (lfHeight > 0)
-        EmHeight64 = (FontGDI->EmHeight << 6) + 31;
-    else
-        EmHeight64 = (FontGDI->EmHeight << 6);
+    EmHeight64 = (FontGDI->EmHeight << 6);
 
     req.type           = FT_SIZE_REQUEST_TYPE_NOMINAL;
     req.width          = 0;
diff --git a/win32ss/user/ntuser/draw.c b/win32ss/user/ntuser/draw.c
index eb97e1e1f16..705229aa7a7 100644
--- a/win32ss/user/ntuser/draw.c
+++ b/win32ss/user/ntuser/draw.c
@@ -820,7 +820,7 @@ BOOL FASTCALL UITOOLS95_DrawFrameCaption(HDC dc, LPRECT r, UINT uFlags)
     lf.lfWidth = 0;
     lf.lfWeight = FW_NORMAL;
     lf.lfCharSet = DEFAULT_CHARSET;
-    lf.lfQuality = NONANTIALIASED_QUALITY;
+    lf.lfQuality = ANTIALIASED_QUALITY;
     RtlCopyMemory(lf.lfFaceName, L"Marlett", sizeof(L"Marlett"));
     hFont = GreCreateFontIndirectW(&lf);
     /* save font and text color */
diff --git a/win32ss/user/user32/windows/draw.c b/win32ss/user/user32/windows/draw.c
index 62798c89b26..15eaf137784 100644
--- a/win32ss/user/user32/windows/draw.c
+++ b/win32ss/user/user32/windows/draw.c
@@ -842,6 +842,7 @@ static BOOL UITOOLS95_DrawFrameCaption(HDC dc, LPRECT r, UINT uFlags)
     lf.lfWidth = 0;
     lf.lfWeight = FW_NORMAL;
     lf.lfCharSet = DEFAULT_CHARSET;
+    lf.lfQuality = ANTIALIASED_QUALITY;
     lstrcpy(lf.lfFaceName, TEXT("Marlett"));
     hFont = CreateFontIndirect(&lf);
     /* save font and text color */