diff --git a/tagstudio/src/core/constants.py b/tagstudio/src/core/constants.py
index 6f67bb2e0..2bd1fc379 100644
--- a/tagstudio/src/core/constants.py
+++ b/tagstudio/src/core/constants.py
@@ -7,6 +7,11 @@
 COLLAGE_FOLDER_NAME: str = "collages"
 LIBRARY_FILENAME: str = "ts_library.json"
 
+FONT_SAMPLE_TEXT: str = (
+    """ABCDEFGHIJKLMNOPQRSTUVWXYZabcdefghijklmnopqrstuvwxyz0123456789!?@$%(){}[]"""
+)
+FONT_SAMPLE_SIZES: list[int] = [10, 15, 20]
+
 # TODO: Turn this whitelist into a user-configurable blacklist.
 IMAGE_TYPES: list[str] = [
     ".png",
@@ -142,6 +147,7 @@
 ]
 PROGRAM_TYPES: list[str] = [".exe", ".app"]
 SHORTCUT_TYPES: list[str] = [".lnk", ".desktop", ".url"]
+FONT_TYPES: list[str] = [".ttf", ".otf", ".woff", ".woff2", ".ttc"]
 
 ALL_FILE_TYPES: list[str] = (
     IMAGE_TYPES
@@ -153,6 +159,7 @@
     + ARCHIVE_TYPES
     + PROGRAM_TYPES
     + SHORTCUT_TYPES
+    + FONT_TYPES
 )
 
 BOX_FIELDS = ["tag_box", "text_box"]
diff --git a/tagstudio/src/qt/helpers/text_wrapper.py b/tagstudio/src/qt/helpers/text_wrapper.py
new file mode 100644
index 000000000..64bd4616d
--- /dev/null
+++ b/tagstudio/src/qt/helpers/text_wrapper.py
@@ -0,0 +1,51 @@
+# Copyright (C) 2024 Travis Abendshien (CyanVoxel).
+# Licensed under the GPL-3.0 License.
+# Created for TagStudio: https://github.com/CyanVoxel/TagStudio
+
+from PIL import Image, ImageDraw, ImageFont
+
+
+def wrap_line(  # type: ignore
+    text: str,
+    font: ImageFont.ImageFont,
+    width: int = 256,
+    draw: ImageDraw.ImageDraw = None,
+) -> int:
+    """
+    Takes in a single line and returns the index it should be broken up at but
+    it only splits one Time
+    """
+    if draw is None:
+        bg = Image.new("RGB", (width, width), color="#1e1e1e")
+        draw = ImageDraw.Draw(bg)
+    if draw.textlength(text, font=font) > width:
+        for i in range(
+            int(len(text) / int(draw.textlength(text, font=font)) * width) - 2,
+            0,
+            -1,
+        ):
+            if draw.textlength(text[:i], font=font) < width:
+                return i
+    else:
+        return -1
+
+
+def wrap_full_text(
+    text: str,
+    font: ImageFont.ImageFont,
+    width: int = 256,
+    draw: ImageDraw.ImageDraw = None,
+) -> str:
+    """
+    Takes in a string and breaks it up to fit in the canvas given accounts for kerning and font size etc.
+    """
+    lines = []
+    i = 0
+    last_i = 0
+    while wrap_line(text[i:], font=font, width=width, draw=draw) > 0:
+        i = wrap_line(text[i:], font=font, width=width, draw=draw) + last_i
+        lines.append(text[last_i:i])
+        last_i = i
+    lines.append(text[last_i:])
+    text_wrapped = "\n".join(lines)
+    return text_wrapped
diff --git a/tagstudio/src/qt/widgets/preview_panel.py b/tagstudio/src/qt/widgets/preview_panel.py
index 209e8df71..6892c7f5e 100644
--- a/tagstudio/src/qt/widgets/preview_panel.py
+++ b/tagstudio/src/qt/widgets/preview_panel.py
@@ -10,7 +10,7 @@
 
 import cv2
 import rawpy
-from PIL import Image, UnidentifiedImageError
+from PIL import Image, UnidentifiedImageError, ImageFont
 from PIL.Image import DecompressionBombError
 from PySide6.QtCore import QModelIndex, Signal, Qt, QSize
 from PySide6.QtGui import QResizeEvent, QAction
@@ -30,7 +30,13 @@
 
 from src.core.enums import SettingItems, Theme
 from src.core.library import Entry, ItemType, Library
-from src.core.constants import VIDEO_TYPES, IMAGE_TYPES, RAW_IMAGE_TYPES, TS_FOLDER_NAME
+from src.core.constants import (
+    VIDEO_TYPES,
+    IMAGE_TYPES,
+    RAW_IMAGE_TYPES,
+    TS_FOLDER_NAME,
+    FONT_TYPES,
+)
 from src.qt.helpers.file_opener import FileOpenerLabel, FileOpenerHelper, open_file
 from src.qt.modals.add_field import AddFieldModal
 from src.qt.widgets.thumb_renderer import ThumbRenderer
@@ -559,6 +565,11 @@ def update_widgets(self):
                             self.dimensions_label.setText(
                                 f"{filepath.suffix.upper()[1:]}  •  {format_size(filepath.stat().st_size)}\n{image.width} x {image.height} px"
                             )
+                        elif filepath.suffix.lower() in FONT_TYPES:
+                            font = ImageFont.truetype(filepath)
+                            self.dimensions_label.setText(
+                                f"{filepath.suffix.upper()[1:]} •  {format_size(filepath.stat().st_size)}\n{font.getname()[0]} ({font.getname()[1]}) "
+                            )
                         else:
                             self.dimensions_label.setText(
                                 f"{filepath.suffix.upper()[1:]}  •  {format_size(filepath.stat().st_size)}"
diff --git a/tagstudio/src/qt/widgets/thumb_renderer.py b/tagstudio/src/qt/widgets/thumb_renderer.py
index 9ed612c98..47421b4f3 100644
--- a/tagstudio/src/qt/widgets/thumb_renderer.py
+++ b/tagstudio/src/qt/widgets/thumb_renderer.py
@@ -23,11 +23,15 @@
 from PySide6.QtCore import QObject, Signal, QSize
 from PySide6.QtGui import QPixmap
 from src.qt.helpers.gradient import four_corner_gradient_background
+from src.qt.helpers.text_wrapper import wrap_full_text
 from src.core.constants import (
     PLAINTEXT_TYPES,
+    FONT_TYPES,
     VIDEO_TYPES,
     IMAGE_TYPES,
     RAW_IMAGE_TYPES,
+    FONT_SAMPLE_TEXT,
+    FONT_SAMPLE_SIZES,
     BLENDER_TYPES,
 )
 from src.core.utils.encoding import detect_char_encoding
@@ -185,7 +189,40 @@ def render(
                         text = text_file.read(256)
                     bg = Image.new("RGB", (256, 256), color="#1e1e1e")
                     draw = ImageDraw.Draw(bg)
-                    draw.text((16, 16), text, file=(255, 255, 255))
+                    draw.text((16, 16), text, fill=(255, 255, 255))
+                    image = bg
+                # Fonts ========================================================
+                elif _filepath.suffix.lower() in FONT_TYPES:
+                    # Scale the sample font sizes to the preview image
+                    # resolution,assuming the sizes are tuned for 256px.
+                    scaled_sizes: list[int] = [
+                        math.floor(x * (adj_size / 256)) for x in FONT_SAMPLE_SIZES
+                    ]
+                    if gradient:
+                        # handles small thumbnails
+                        bg = Image.new("RGB", (adj_size, adj_size), color="#1e1e1e")
+                        draw = ImageDraw.Draw(bg)
+                        font = ImageFont.truetype(
+                            _filepath, size=math.ceil(adj_size * 0.65)
+                        )
+                        draw.text((10, 0), "Aa", font=font)
+                    else:
+                        # handles big thumbnails and renders a sample text in multiple font sizes
+                        bg = Image.new("RGB", (adj_size, adj_size), color="#1e1e1e")
+                        draw = ImageDraw.Draw(bg)
+                        lines_of_padding = 2
+                        y_offset = 0
+
+                        for font_size in scaled_sizes:
+                            font = ImageFont.truetype(_filepath, size=font_size)
+                            text_wrapped: str = wrap_full_text(
+                                FONT_SAMPLE_TEXT, font=font, width=adj_size, draw=draw
+                            )
+                            draw.multiline_text((0, y_offset), text_wrapped, font=font)
+                            y_offset += (
+                                len(text_wrapped.split("\n")) + lines_of_padding
+                            ) * draw.textbbox((0, 0), "A", font=font)[-1]
+
                     image = bg
                 # 3D ===========================================================
                 # elif extension == 'stl':