diff --git "a/win32ss/gdi/ntgdi/freetype.c" "b/win32ss/gdi/ntgdi/freetype.c"
index 43547c20249..8a50bd8374b 100644
--- "a/win32ss/gdi/ntgdi/freetype.c"
+++ "b/win32ss/gdi/ntgdi/freetype.c"
@@ -1645,6 +1645,85 @@ UINT FASTCALL IntGetCharSet(INT nIndex, FT_ULong CodePageRange1)
 /* pixels to points */
 #define PX2PT(pixels) FT_MulDiv((pixels), 72, 96)
 
+/* Borrowed and adapted from Wine */
+static BOOL select_charmap(FT_Face ft_face, FT_Encoding encoding)
+{
+    FT_Error ft_err = FT_Err_Invalid_CharMap_Handle;
+    FT_CharMap cmap0, cmap1, cmap2, cmap3, cmap_def;
+    FT_Int i;
+
+    cmap0 = cmap1 = cmap2 = cmap3 = cmap_def = NULL;
+
+    for (i = 0; i < ft_face->num_charmaps; i++)
+    {
+        if (ft_face->charmaps[i]->encoding == encoding)
+        {
+            switch (ft_face->charmaps[i]->platform_id)
+            {
+                default:
+                    cmap_def = ft_face->charmaps[i];
+                    break;
+                case 0: /* Apple Unicode */
+                    cmap0 = ft_face->charmaps[i];
+                    break;
+                case 1: /* Macintosh */
+                    cmap1 = ft_face->charmaps[i];
+                    break;
+                case 2: /* ISO */
+                    cmap2 = ft_face->charmaps[i];
+                    break;
+                case 3: /* Microsoft */
+                    cmap3 = ft_face->charmaps[i];
+                    break;
+            }
+        }
+#ifdef __REACTOS__
+// Wine bug: for each loop iteration, a FT_Set_Charmap() call is made.
+// ReactOS fix: Instead, loop until we retrieve all the cmap pointers
+// of interest, then do one single FT_Set_Charmap() call using the
+// preferred cmap.
+    }{
+#endif
+
+        if (cmap3) /* prefer Microsoft cmap table */
+            ft_err = FT_Set_Charmap(ft_face, cmap3);
+        else if (cmap1)
+            ft_err = FT_Set_Charmap(ft_face, cmap1);
+        else if (cmap2)
+            ft_err = FT_Set_Charmap(ft_face, cmap2);
+        else if (cmap0)
+            ft_err = FT_Set_Charmap(ft_face, cmap0);
+        else if (cmap_def)
+            ft_err = FT_Set_Charmap(ft_face, cmap_def);
+    }
+
+    return ft_err == FT_Err_Ok;
+}
+
+/* Borrowed from Wine */
+static FT_Encoding pick_charmap( FT_Face face, int charset )
+{
+    static const FT_Encoding regular_order[] = { FT_ENCODING_UNICODE, FT_ENCODING_APPLE_ROMAN, FT_ENCODING_MS_SYMBOL, 0 };
+    static const FT_Encoding symbol_order[]  = { FT_ENCODING_MS_SYMBOL, FT_ENCODING_UNICODE, FT_ENCODING_APPLE_ROMAN, 0 };
+    const FT_Encoding *encs = regular_order;
+
+    if (charset == SYMBOL_CHARSET) encs = symbol_order;
+
+    while (*encs != 0)
+    {
+        if (select_charmap( face, *encs )) break;
+        encs++;
+    }
+
+    if (!face->charmap && face->num_charmaps)
+    {
+        if (!FT_Set_Charmap(face, face->charmaps[0]))
+            return face->charmap->encoding;
+    }
+
+    return *encs;
+}
+
 static INT FASTCALL
 IntGdiLoadFontsFromMemory(PGDI_LOAD_FONT pLoadFont,
                           PSHARED_FACE SharedFace, FT_Long FontIndex, INT CharSetIndex)
@@ -1961,6 +2040,24 @@ IntGdiLoadFontByIndexFromMemory(PGDI_LOAD_FONT pLoadFont, FT_Long FontIndex)
         return 0; /* Failure */
     }
 
+    /*
+     * In IntGdiLoadFontsFromMemory, when CharSetIndex == -1,
+     * we will always activate a charmap in the font face.
+     *
+     * Note from FreeType documentation:
+     * https://freetype.org/freetype2/docs/reference/ft2-character_mapping.html#ft_charmap
+     *
+     * When a new face is created (either through FT_New_Face or
+     * FT_Open_Face), the library looks for a Unicode charmap within
+     * the list and automatically activates it. If there is no
+     * Unicode charmap, FreeType doesn't set an 'active' charmap.
+     */
+    pick_charmap(Face, DEFAULT_CHARSET);
+    if (!Face->charmap)
+    {
+        DPRINT1("WARNING: Could not find default charmap!\n");
+    }
+
     pLoadFont->IsTrueType = FT_IS_SFNT(Face);
     num_faces = Face->num_faces;
     SharedFace = SharedFace_Create(Face, pLoadFont->Memory);