diff --git a/components/system/Files/FileEntry/RenameBox.tsx b/components/system/Files/FileEntry/RenameBox.tsx
index e67e15d5..67afe311 100644
--- a/components/system/Files/FileEntry/RenameBox.tsx
+++ b/components/system/Files/FileEntry/RenameBox.tsx
@@ -1,7 +1,9 @@
+import { getLineCount } from "components/system/Files/FileEntry/functions";
 import { haltEvent } from "components/system/Files/FileManager/functions";
 import StyledRenameBox from "components/system/Files/Views/StyledRenameBox";
 import { extname } from "path";
-import { useEffect, useRef } from "react";
+import { useCallback, useEffect, useRef } from "react";
+import { useTheme } from "styled-components";
 import { PREVENT_SCROLL } from "utils/constants";
 
 type RenameBoxProps = {
@@ -13,11 +15,31 @@ type RenameBoxProps = {
 const RenameBox = ({ name, path, renameFile }: RenameBoxProps): JSX.Element => {
   const inputRef = useRef<HTMLTextAreaElement | null>(null);
   const saveRename = (): void => renameFile(path, inputRef.current?.value);
+  const { formats, sizes } = useTheme();
+  const updateRows = useCallback(
+    (text: string): void => {
+      const lines = getLineCount(
+        text,
+        sizes.fileEntry.fontSize,
+        formats.systemFont,
+        sizes.fileEntry.renameWidth - sizes.fileEntry.renamePadding * 2
+      );
+
+      inputRef.current?.setAttribute("rows", lines.toString());
+    },
+    [
+      formats.systemFont,
+      sizes.fileEntry.fontSize,
+      sizes.fileEntry.renamePadding,
+      sizes.fileEntry.renameWidth,
+    ]
+  );
 
   useEffect(() => {
     inputRef.current?.focus(PREVENT_SCROLL);
     inputRef.current?.setSelectionRange(0, name.length - extname(name).length);
-  }, [name]);
+    updateRows(name);
+  }, [name, updateRows]);
 
   return (
     <StyledRenameBox
@@ -25,7 +47,13 @@ const RenameBox = ({ name, path, renameFile }: RenameBoxProps): JSX.Element => {
       onBlurCapture={saveRename}
       onClick={haltEvent}
       onKeyDown={({ key }) => key === "Enter" && saveRename()}
-      onKeyUp={haltEvent}
+      onKeyUp={(event) => {
+        if (event.target instanceof HTMLTextAreaElement) {
+          updateRows(event.target.value);
+        }
+
+        haltEvent(event);
+      }}
       ref={inputRef}
     />
   );
diff --git a/components/system/Files/FileEntry/functions.ts b/components/system/Files/FileEntry/functions.ts
index e0e922ee..19ede4ca 100644
--- a/components/system/Files/FileEntry/functions.ts
+++ b/components/system/Files/FileEntry/functions.ts
@@ -176,3 +176,37 @@ export const filterSystemFiles =
   (directory: string) =>
   (file: string): boolean =>
     !SYSTEM_PATHS.has(join(directory, file)) && !SYSTEM_FILES.has(file);
+
+export const getLineCount = (
+  text: string,
+  fontSize: string,
+  fontFamily: string,
+  maxWidth: number
+): number => {
+  const canvas = document.createElement("canvas");
+  const context = canvas.getContext("2d", {
+    alpha: false,
+    desynchronized: true,
+  }) as CanvasRenderingContext2D;
+
+  context.font = `${fontSize} ${fontFamily}`;
+
+  if (context.measureText(text).width > maxWidth) {
+    const lines = [""];
+
+    [...text].forEach((character) => {
+      const lineCount = lines.length - 1;
+      const lineText = `${lines[lineCount]}${character}`;
+
+      if (context.measureText(lineText).width > maxWidth) {
+        lines.push(character);
+      } else {
+        lines[lineCount] = lineText;
+      }
+    });
+
+    return lines.length;
+  }
+
+  return 1;
+};
diff --git a/components/system/Files/FileManager/index.tsx b/components/system/Files/FileManager/index.tsx
index 1a1f80d4..d4f53574 100644
--- a/components/system/Files/FileManager/index.tsx
+++ b/components/system/Files/FileManager/index.tsx
@@ -17,6 +17,7 @@ import { MOUNTABLE_EXTENSIONS, SHORTCUT_EXTENSION } from "utils/constants";
 type FileManagerProps = {
   closing?: boolean;
   hideLoading?: boolean;
+  hideScrolling?: boolean;
   url: string;
   view: FileManagerViewNames;
 };
@@ -24,6 +25,7 @@ type FileManagerProps = {
 const FileManager = ({
   closing,
   hideLoading,
+  hideScrolling,
   url,
   view,
 }: FileManagerProps): JSX.Element => {
@@ -60,6 +62,7 @@ const FileManager = ({
   ) : (
     <StyledFileManager
       ref={fileManagerRef}
+      scrollable={!hideScrolling}
       selecting={isSelecting}
       {...selectionEvents}
       {...fileDrop}
diff --git a/components/system/Files/Views/Icon/StyledFileManager.ts b/components/system/Files/Views/Icon/StyledFileManager.ts
index 83f14239..5d2f638e 100644
--- a/components/system/Files/Views/Icon/StyledFileManager.ts
+++ b/components/system/Files/Views/Icon/StyledFileManager.ts
@@ -14,6 +14,7 @@ const StyledFileManager = styled.ol<StyledFileManagerProps>`
   grid-template-rows: ${({ theme }) =>
     `repeat(auto-fill, ${theme.sizes.fileManager.gridEntryHeight})`};
   height: ${({ theme }) => `calc(100% - ${theme.sizes.taskbar.height})`};
+  overflow: ${({ scrollable }) => (scrollable ? undefined : "hidden")};
   padding: ${({ theme }) => theme.sizes.fileManager.padding};
   pointer-events: ${({ selecting }) => (selecting ? "auto" : undefined)};
   row-gap: ${({ theme }) => theme.sizes.fileManager.rowGap};
diff --git a/components/system/Files/Views/StyledRenameBox.ts b/components/system/Files/Views/StyledRenameBox.ts
index 758f4b63..bece9d3f 100644
--- a/components/system/Files/Views/StyledRenameBox.ts
+++ b/components/system/Files/Views/StyledRenameBox.ts
@@ -9,12 +9,13 @@ const StyledRenameBox = styled.textarea.attrs({
   font-family: inherit;
   font-size: 11.5px;
   margin-bottom: 2px;
-  padding: 1px 5px;
+  overflow: hidden;
+  padding: ${({ theme }) => `1px ${theme.sizes.fileEntry.renamePadding}px`};
   position: relative;
   resize: none;
   text-align: center;
   top: 2px;
-  width: 70px;
+  width: ${({ theme }) => `${theme.sizes.fileEntry.renameWidth}px`};
 `;
 
 export default StyledRenameBox;
diff --git a/components/system/Files/Views/index.ts b/components/system/Files/Views/index.ts
index 812accd3..f5e6db8e 100644
--- a/components/system/Files/Views/index.ts
+++ b/components/system/Files/Views/index.ts
@@ -10,6 +10,7 @@ export type StyledFileEntryProps = {
 };
 
 export type StyledFileManagerProps = {
+  scrollable: boolean;
   selecting: boolean;
 };
 
diff --git a/pages/index.tsx b/pages/index.tsx
index 1a770040..5e7ba4e4 100644
--- a/pages/index.tsx
+++ b/pages/index.tsx
@@ -11,7 +11,12 @@ const Home = (): React.ReactElement => {
 
   return (
     <Desktop>
-      <FileManager url="/Users/Public/Desktop" view="icon" hideLoading />
+      <FileManager
+        url="/Users/Public/Desktop"
+        view="icon"
+        hideLoading
+        hideScrolling
+      />
       <Taskbar />
       <AppsLoader />
     </Desktop>
diff --git a/styles/GlobalStyle.ts b/styles/GlobalStyle.ts
index 939bc73c..113ce787 100644
--- a/styles/GlobalStyle.ts
+++ b/styles/GlobalStyle.ts
@@ -13,7 +13,7 @@ const GlobalStyle = createGlobalStyle`
   }
 
   body {
-    font-family: system-ui, -apple-system, BlinkMacSystemFont, 'Segoe UI', Roboto, Oxygen, Ubuntu, Cantarell, 'Open Sans', 'Helvetica Neue', sans-serif;
+    font-family: ${({ theme }) => theme.formats.systemFont};
     overflow: hidden;
   }
 
diff --git a/styles/defaultTheme/formats.ts b/styles/defaultTheme/formats.ts
index 3b65b3ec..e51c828d 100644
--- a/styles/defaultTheme/formats.ts
+++ b/styles/defaultTheme/formats.ts
@@ -15,6 +15,8 @@ const formats = {
     minute: "2-digit",
     hour12: true,
   } as Intl.DateTimeFormatOptions,
+  systemFont:
+    "system-ui, -apple-system, BlinkMacSystemFont, 'Segoe UI', Roboto, Oxygen, Ubuntu, Cantarell, 'Open Sans', 'Helvetica Neue', sans-serif",
 };
 
 export default formats;
diff --git a/styles/defaultTheme/sizes.ts b/styles/defaultTheme/sizes.ts
index c346aae7..81ca4502 100644
--- a/styles/defaultTheme/sizes.ts
+++ b/styles/defaultTheme/sizes.ts
@@ -9,6 +9,8 @@ const sizes = {
   fileEntry: {
     fontSize: "12px",
     iconSize: "48px",
+    renamePadding: 5,
+    renameWidth: 75,
   },
   fileManager: {
     columnGap: "1px",