diff --git a/docs/guide/types/_commonInnerLabel.md b/docs/guide/types/_commonInnerLabel.md
index b193ba977..746b448fa 100644
--- a/docs/guide/types/_commonInnerLabel.md
+++ b/docs/guide/types/_commonInnerLabel.md
@@ -19,6 +19,7 @@ All of these options can be [Scriptable](../options.md#scriptable-options)
 | `textAlign` | `string` | `'start'` | Text alignment of label content when there's more than one line. Possible options are: `'left'`, `'start'`, `'center'`, `'end'`, `'right'`.
 | `textStrokeColor` | [`Color`](../options.md#color) | `undefined` | The color of the stroke around the text.
 | `textStrokeWidth` | `number` | `0` | Stroke width around the text.
+| `textWrap` | `boolean` | `false` | If `true` and the content label overflows the size of the box, the label has been splitted in multiple lines to be drawn in the box. This options is applicable only on `'box'` annotation.
 | `width` | `number`\|`string` | `undefined` | Overrides the width of the image or canvas element. Could be set in pixel by a number, or in percentage of current width of image or canvas element by a string. If undefined, uses the width of the image or canvas element. It is used only when the content is an image or canvas element.
 | `xAdjust` | `number` | `0` | Adjustment along x-axis (left-right) of label relative to computed position. Negative values move the label left, positive right.
 | `yAdjust` | `number` | `0` | Adjustment along y-axis (top-bottom) of label relative to computed position. Negative values move the label up, positive down.
diff --git a/src/helpers/helpers.canvas.js b/src/helpers/helpers.canvas.js
index 436902b8b..f0a1cfaa8 100644
--- a/src/helpers/helpers.canvas.js
+++ b/src/helpers/helpers.canvas.js
@@ -1,13 +1,19 @@
-import {addRoundedRectPath, isArray, isNumber, toFont, toTRBLCorners, toRadians, PI, TAU, HALF_PI, QUARTER_PI, TWO_THIRDS_PI, RAD_PER_DEG} from 'chart.js/helpers';
+import {addRoundedRectPath, isArray, isNumber, toFont, toPadding, toTRBLCorners, toRadians, PI, TAU, HALF_PI, QUARTER_PI, TWO_THIRDS_PI, RAD_PER_DEG} from 'chart.js/helpers';
 import {clampAll, clamp} from './helpers.core';
 import {calculateTextAlignment, getSize} from './helpers.options';
 
+const BLANK = ' ';
 const widthCache = new Map();
 const notRadius = (radius) => isNaN(radius) || radius <= 0;
 const fontsKey = (fonts) => fonts.reduce(function(prev, item) {
   prev += item.string;
   return prev;
 }, '');
+const getContent = (content, wrappedText) => wrappedText
+  ? wrappedText
+  : isArray(content)
+    ? content
+    : [content];
 
 /**
  * @typedef { import('chart.js').Point } Point
@@ -94,6 +100,23 @@ export function measureLabelSize(ctx, options) {
   return widthCache.get(mapKey);
 }
 
+/**
+ * @param {CanvasRenderingContext2D} ctx
+ * @param {{width: number}} properties
+ * @param {CoreLabelOptions} options
+ * @returns {{width: number, height: number}}
+ */
+export function measureWrappedLabelSize(ctx, properties, options) {
+  const wrappedOptions = wrapLabel(ctx, properties, options);
+  const result = measureLabelSize(ctx, {
+    content: wrappedOptions.content,
+    font: wrappedOptions.font,
+    textStrokeWidth: options.textStrokeWidth
+  });
+  result.wrappedOptions = wrappedOptions;
+  return result;
+}
+
 /**
  * @param {CanvasRenderingContext2D} ctx
  * @param {{x: number, y: number, width: number, height: number}} rect
@@ -121,7 +144,7 @@ export function drawBox(ctx, rect, options) {
 
 /**
  * @param {CanvasRenderingContext2D} ctx
- * @param {{x: number, y: number, width: number, height: number}} rect
+ * @param {{x: number, y: number, width: number, height: number, _wrappedOptions: object|undefined}} rect
  * @param {CoreLabelOptions} options
  */
 export function drawLabel(ctx, rect, options) {
@@ -133,10 +156,11 @@ export function drawLabel(ctx, rect, options) {
     ctx.restore();
     return;
   }
-  const labels = isArray(content) ? content : [content];
-  const optFont = options.font;
+  const wrapOpt = rect._wrappedOptions || {};
+  const labels = getContent(content, wrapOpt.content);
+  const optFont = wrapOpt.font || options.font;
   const fonts = isArray(optFont) ? optFont.map(f => toFont(f)) : [toFont(optFont)];
-  const optColor = options.color;
+  const optColor = wrapOpt.color || options.color;
   const colors = isArray(optColor) ? optColor : [optColor];
   const x = calculateTextAlignment(rect, options);
   const y = rect.y + options.textStrokeWidth / 2;
@@ -329,3 +353,68 @@ function getOpacity(value, elementValue) {
   const opacity = isNumber(value) ? value : elementValue;
   return isNumber(opacity) ? clamp(opacity, 0, 1) : 1;
 }
+
+function wrapLabel(ctx, properties, options) {
+  const padding = toPadding(options.padding);
+  const maxWidth = properties.width - padding.left - padding.right - options.borderWidth;
+  const content = options.content;
+  const text = isArray(content) ? content : [content];
+  const optFont = options.font;
+  const fonts = isArray(optFont) ? optFont : [optFont];
+  const optColor = options.color;
+  const colors = isArray(optColor) ? optColor : [optColor];
+  ctx.save();
+  const result = scanLabelLines(ctx, text, maxWidth, {fonts, colors});
+  ctx.restore();
+  return result;
+}
+
+function scanLabelLines(ctx, text, maxWidth, {fonts, colors}) {
+  const result = {
+    content: [],
+    font: [],
+    color: []
+  };
+  text.forEach(function(line, index) {
+    const normLine = line + '';
+    const c = colors[Math.min(index, colors.length - 1)];
+    const f = fonts[Math.min(index, fonts.length - 1)];
+    const font = toFont(f);
+    ctx.font = font.string;
+    const width = ctx.measureText(normLine).width;
+    if (maxWidth >= width || !normLine.includes(BLANK)) {
+      result.content.push(normLine);
+      result.font.push(f);
+      result.color.push(c);
+    } else {
+      const wrappedLine = splitLabel(ctx, normLine, maxWidth);
+      result.content.push(...wrappedLine);
+      result.font.push(...wrappedLine.map(() => f));
+      result.color.push(...wrappedLine.map(() => c));
+    }
+  });
+  return result;
+}
+
+function splitLabel(ctx, text, maxWidth) {
+  const sepaWidth = ctx.measureText(BLANK).width;
+  const result = [];
+  const words = text.split(BLANK);
+  let temp = '';
+  let current = 0;
+  for (const w of words) {
+    const wWidth = ctx.measureText(w).width;
+    if ((current + wWidth + sepaWidth) <= maxWidth) {
+      temp += w + BLANK;
+      current += wWidth + sepaWidth;
+    } else {
+      result.push(temp.trim());
+      temp = w + BLANK;
+      current = wWidth + sepaWidth;
+    }
+  }
+  if (temp.length) {
+    result.push(temp.trim());
+  }
+  return result;
+}
diff --git a/src/helpers/helpers.chart.js b/src/helpers/helpers.chart.js
index 76ab085c6..3ae792d09 100644
--- a/src/helpers/helpers.chart.js
+++ b/src/helpers/helpers.chart.js
@@ -1,11 +1,12 @@
 import {isFinite, toPadding} from 'chart.js/helpers';
-import {measureLabelSize} from './helpers.canvas';
+import {measureLabelSize, measureWrappedLabelSize, isImageOrCanvas} from './helpers.canvas';
 import {isBoundToPoint, getRelativePosition, toPosition, initAnimationProperties} from './helpers.options';
 
 const limitedLineScale = {
   xScaleID: {min: 'xMin', max: 'xMax', start: 'left', end: 'right', startProp: 'x', endProp: 'x2'},
   yScaleID: {min: 'yMin', max: 'yMax', start: 'bottom', end: 'top', startProp: 'y', endProp: 'y2'}
 };
+const isTextToWrap = (options) => options.type === 'box' && options.label.textWrap && !isImageOrCanvas(options.content);
 
 /**
  * @typedef { import("chart.js").Chart } Chart
@@ -270,7 +271,7 @@ function resolveLabelElementProperties(chart, properties, options) {
   label.callout.display = false;
   const position = toPosition(label.position);
   const padding = toPadding(label.padding);
-  const labelSize = measureLabelSize(chart.ctx, label);
+  const labelSize = isTextToWrap(options) ? measureWrappedLabelSize(chart.ctx, properties, label) : measureLabelSize(chart.ctx, label);
   const x = calculateX({properties, options}, labelSize, position, padding);
   const y = calculateY({properties, options}, labelSize, position, padding);
   const width = labelSize.width + padding.width;
@@ -284,7 +285,8 @@ function resolveLabelElementProperties(chart, properties, options) {
     height,
     centerX: x + width / 2,
     centerY: y + height / 2,
-    rotation: label.rotation
+    rotation: label.rotation,
+    _wrappedOptions: labelSize.wrappedOptions
   };
 
 }
diff --git a/src/types/box.js b/src/types/box.js
index 66d02ae95..e78299f31 100644
--- a/src/types/box.js
+++ b/src/types/box.js
@@ -68,6 +68,7 @@ BoxAnnotation.defaults = {
     textAlign: 'start',
     textStrokeColor: undefined,
     textStrokeWidth: 0,
+    textWrap: false,
     width: undefined,
     xAdjust: 0,
     yAdjust: 0,
diff --git a/src/types/label.js b/src/types/label.js
index f1c03ce2a..3d3d6104b 100644
--- a/src/types/label.js
+++ b/src/types/label.js
@@ -244,10 +244,11 @@ function resolveCalloutAutoPosition(element, options) {
   return result.sort((a, b) => a.distance - b.distance)[0].position;
 }
 
-function getLabelSize({x, y, width, height, options}) {
+function getLabelSize({x, y, width, height, _wrappedOptions, options}) {
   const hBorderWidth = options.borderWidth / 2;
   const padding = toPadding(options.padding);
   return {
+    _wrappedOptions,
     x: x + padding.left + hBorderWidth,
     y: y + padding.top + hBorderWidth,
     width: width - padding.left - padding.right - options.borderWidth,
diff --git a/test/fixtures/box/labelDecoration.js b/test/fixtures/box/labelDecoration.js
index 6603baffa..131886fd4 100644
--- a/test/fixtures/box/labelDecoration.js
+++ b/test/fixtures/box/labelDecoration.js
@@ -1,5 +1,5 @@
 module.exports = {
-  tolerance: 0.0315,
+  tolerance: 0.0316,
   config: {
     type: 'scatter',
     options: {
diff --git a/test/fixtures/box/labelWrap.js b/test/fixtures/box/labelWrap.js
new file mode 100644
index 000000000..625ef1d42
--- /dev/null
+++ b/test/fixtures/box/labelWrap.js
@@ -0,0 +1,68 @@
+module.exports = {
+  tolerance: 0.0075,
+  config: {
+    type: 'bar',
+    options: {
+      scales: {
+        x: {
+          display: false,
+          labels: ['January', 'February', 'March', 'April', 'May', 'June', 'July'],
+        },
+        y: {
+          display: false,
+          min: 0,
+          max: 25
+        }
+      },
+      plugins: {
+        annotation: {
+          annotations: {
+            box1: {
+              type: 'box',
+              xMin: -0.5,
+              xMax: 2,
+              yMin: 0,
+              yMax: 5,
+              backgroundColor: 'rgba(255, 99, 132, 0.5)',
+              label: {
+                display: true,
+                content: 'This is a long label - '.repeat(4),
+                textWrap: true,
+              }
+            },
+            box2: {
+              type: 'box',
+              xMin: 2.5,
+              xMax: 5,
+              yMin: 0,
+              yMax: 5,
+              backgroundColor: 'rgba(255, 99, 132, 0.5)',
+              label: {
+                display: true,
+                content: ['No wrap!', 'This is a long label - '.repeat(4), 'No wrap!'],
+                textWrap: true,
+              }
+            },
+            box3: {
+              type: 'box',
+              xMin: 1,
+              xMax: 5,
+              yMin: 15,
+              yMax: 20,
+              backgroundColor: 'rgba(255, 99, 132, 0.5)',
+              label: {
+                display: true,
+                content: ['No wrap!', 'Overflow ' + 'This is a long label - '.repeat(3), 'No wrap!'],
+                textWrap: false,
+                textAlign: 'center'
+              }
+            },
+          }
+        }
+      }
+    }
+  },
+  options: {
+    spriteText: true
+  }
+};
diff --git a/test/fixtures/box/labelWrap.png b/test/fixtures/box/labelWrap.png
new file mode 100644
index 000000000..e5d022cf0
Binary files /dev/null and b/test/fixtures/box/labelWrap.png differ
diff --git a/test/fixtures/box/labelWrapMultiColors.js b/test/fixtures/box/labelWrapMultiColors.js
new file mode 100644
index 000000000..751a0769d
--- /dev/null
+++ b/test/fixtures/box/labelWrapMultiColors.js
@@ -0,0 +1,53 @@
+module.exports = {
+  tolerance: 0.0137,
+  config: {
+    type: 'bar',
+    options: {
+      scales: {
+        x: {
+          display: false,
+          labels: ['January', 'February', 'March', 'April', 'May', 'June', 'July'],
+        },
+        y: {
+          display: false,
+          min: 0,
+          max: 25
+        }
+      },
+      plugins: {
+        annotation: {
+          annotations: {
+            box1: {
+              type: 'box',
+              xMin: 2,
+              xMax: 5,
+              yMin: 1,
+              yMax: 6,
+              backgroundColor: 'rgba(255, 99, 132, 0.5)',
+              label: {
+                display: true,
+                content: 'This is a long label - '.repeat(4),
+                textWrap: true,
+                color: ['green', 'white', 'blue']
+              }
+            },
+            box2: {
+              type: 'box',
+              xMin: 2,
+              xMax: 5,
+              yMin: 10,
+              yMax: 15,
+              backgroundColor: 'rgba(255, 99, 132, 0.5)',
+              label: {
+                display: true,
+                content: ['No wrap!', 'This is a long label - '.repeat(4), 'No wrap!'],
+                textWrap: true,
+                color: ['blank', 'green', 'blue']
+              }
+            }
+          }
+        }
+      }
+    }
+  }
+};
diff --git a/test/fixtures/box/labelWrapMultiColors.png b/test/fixtures/box/labelWrapMultiColors.png
new file mode 100644
index 000000000..083de59dd
Binary files /dev/null and b/test/fixtures/box/labelWrapMultiColors.png differ
diff --git a/test/fixtures/box/labelWrapMultiFonts.js b/test/fixtures/box/labelWrapMultiFonts.js
new file mode 100644
index 000000000..80b67a240
--- /dev/null
+++ b/test/fixtures/box/labelWrapMultiFonts.js
@@ -0,0 +1,53 @@
+module.exports = {
+  tolerance: 0.0135,
+  config: {
+    type: 'bar',
+    options: {
+      scales: {
+        x: {
+          display: false,
+          labels: ['January', 'February', 'March', 'April', 'May', 'June', 'July'],
+        },
+        y: {
+          display: false,
+          min: 0,
+          max: 25
+        }
+      },
+      plugins: {
+        annotation: {
+          annotations: {
+            box1: {
+              type: 'box',
+              xMin: 2,
+              xMax: 5,
+              yMin: 1,
+              yMax: 6,
+              backgroundColor: 'rgba(255, 99, 132, 0.5)',
+              label: {
+                display: true,
+                content: 'This is a long label - '.repeat(4),
+                textWrap: true,
+                font: [{size: 16}, {size: 20}, {size: 24}]
+              }
+            },
+            box2: {
+              type: 'box',
+              xMin: 2,
+              xMax: 5,
+              yMin: 10,
+              yMax: 15,
+              backgroundColor: 'rgba(255, 99, 132, 0.5)',
+              label: {
+                display: true,
+                content: ['No wrap!', 'This is a long label - '.repeat(4), 'No wrap!'],
+                textWrap: true,
+                font: [{size: 24}, {size: 12}, {size: 16}]
+              }
+            }
+          }
+        }
+      }
+    }
+  }
+};
diff --git a/test/fixtures/box/labelWrapMultiFonts.png b/test/fixtures/box/labelWrapMultiFonts.png
new file mode 100644
index 000000000..0ccbaf43a
Binary files /dev/null and b/test/fixtures/box/labelWrapMultiFonts.png differ
diff --git a/test/fixtures/ellipse/labelDecoration.js b/test/fixtures/ellipse/labelDecoration.js
index 19330834b..61351711f 100644
--- a/test/fixtures/ellipse/labelDecoration.js
+++ b/test/fixtures/ellipse/labelDecoration.js
@@ -1,5 +1,5 @@
 module.exports = {
-  tolerance: 0.0320,
+  tolerance: 0.0321,
   config: {
     type: 'scatter',
     options: {
diff --git a/test/fixtures/ellipse/labelWrap.js b/test/fixtures/ellipse/labelWrap.js
new file mode 100644
index 000000000..a21ac4e4e
--- /dev/null
+++ b/test/fixtures/ellipse/labelWrap.js
@@ -0,0 +1,54 @@
+module.exports = {
+  tolerance: 0.0075,
+  config: {
+    type: 'bar',
+    options: {
+      scales: {
+        x: {
+          display: false,
+          labels: ['January', 'February', 'March', 'April', 'May', 'June', 'July'],
+        },
+        y: {
+          display: false,
+          min: 0,
+          max: 25
+        }
+      },
+      plugins: {
+        annotation: {
+          annotations: {
+            box1: {
+              type: 'ellipse',
+              xMin: 2,
+              xMax: 5,
+              yMin: 0,
+              yMax: 5,
+              backgroundColor: 'rgba(255, 99, 132, 0.5)',
+              label: {
+                display: true,
+                content: 'No wrap because ellipse - '.repeat(2),
+                textWrap: true,
+              }
+            },
+            box2: {
+              type: 'ellipse',
+              xMin: 2,
+              xMax: 5,
+              yMin: 10,
+              yMax: 15,
+              backgroundColor: 'rgba(255, 99, 132, 0.5)',
+              label: {
+                display: true,
+                content: ['No wrap!', 'No wrap because ellipse - '.repeat(2), 'No wrap!'],
+                textWrap: true,
+              }
+            },
+          }
+        }
+      }
+    }
+  },
+  options: {
+    spriteText: true
+  }
+};
diff --git a/test/fixtures/ellipse/labelWrap.png b/test/fixtures/ellipse/labelWrap.png
new file mode 100644
index 000000000..e943bc90a
Binary files /dev/null and b/test/fixtures/ellipse/labelWrap.png differ
diff --git a/types/label.d.ts b/types/label.d.ts
index 4c66511f2..0f9d9cba2 100644
--- a/types/label.d.ts
+++ b/types/label.d.ts
@@ -141,6 +141,7 @@ export interface BoxLabelOptions extends CoreLabelOptions {
    * @default true
    */
   display?: Scriptable<boolean, PartialEventContext>,
+  textWrap?: Scriptable<boolean, PartialEventContext>,
   rotation?: Scriptable<number, PartialEventContext>
 }