diff --git a/Packages/ohif-core/client/lib/cornerstone.js b/Packages/ohif-core/client/lib/cornerstone.js
index dfba6b81c..216af4ad6 100644
--- a/Packages/ohif-core/client/lib/cornerstone.js
+++ b/Packages/ohif-core/client/lib/cornerstone.js
@@ -36,9 +36,16 @@ OHIF.cornerstone.repositionTextBox = (eventData, measurementData) => {
 
     const element = eventData.element;
     const enabledElement = cornerstone.getEnabledElement(element);
-    const $element = $(element);
     const image = enabledElement.image;
 
+    const allowedBorders = OHIF.uiSettings.autoPositionMeasurementsTextCallOuts;
+    const allow = {
+        T: !allowedBorders || _.contains(allowedBorders, 'T'),
+        R: !allowedBorders || _.contains(allowedBorders, 'R'),
+        B: !allowedBorders || _.contains(allowedBorders, 'B'),
+        L: !allowedBorders || _.contains(allowedBorders, 'L')
+    };
+
     const getAvailableBlankAreas = (enabledElement, labelWidth, labelHeight) => {
         const { element, canvas, image } = enabledElement;
 
@@ -57,10 +64,10 @@ OHIF.cornerstone.repositionTextBox = (eventData, measurementData) => {
         const canvasHeight = $canvas.outerHeight();
 
         const result = {};
-        result['x-1'] = topLeft.x > labelWidth;
-        result['y-1'] = topLeft.y > labelHeight;
-        result.x1 = canvasWidth - bottomRight.x > labelWidth;
-        result.y1 = canvasHeight - bottomRight.y > labelHeight;
+        result['x-1'] = allow.L && (topLeft.x > labelWidth);
+        result['y-1'] = allow.T && (topLeft.y > labelHeight);
+        result.x1 = allow.R && (canvasWidth - bottomRight.x > labelWidth);
+        result.y1 = allow.B && (canvasHeight - bottomRight.y > labelHeight);
 
         return result;
     };
@@ -76,7 +83,25 @@ OHIF.cornerstone.repositionTextBox = (eventData, measurementData) => {
 
         const diffX = directions.x < 0 ? tool.x : limits.x - tool.x;
         const diffY = directions.y < 0 ? tool.y : limits.y - tool.y;
-        const cornerAxis = diffY < diffX ? 'y' : 'x';
+        let cornerAxis = diffY < diffX ? 'y' : 'x';
+
+        const map = {
+            'x-1': 'L',
+            'y-1': 'T',
+            x1: 'R',
+            y1: 'B'
+        };
+
+        let current = 0;
+        while (current < 4 && !allow[map[cornerAxis + directions[cornerAxis]]]) {
+            // Invert the direction for the next iteration
+            directions[cornerAxis] *= -1;
+
+            // Invert the tempCornerAxis
+            cornerAxis = cornerAxis === 'x' ? 'y' : 'x';
+
+            current++;
+        }
 
         return {
             directions,
diff --git a/Packages/ohif-study-list/both/schema/servers.js b/Packages/ohif-study-list/both/schema/servers.js
index bc503bd22..bc4bd2111 100644
--- a/Packages/ohif-study-list/both/schema/servers.js
+++ b/Packages/ohif-study-list/both/schema/servers.js
@@ -153,6 +153,11 @@ export const UISettings = new SimpleSchema({
         type: Boolean,
         label: 'Enable cine dialog enhancements for multiframe images.',
         defaultValue: false
+    },
+    autoPositionMeasurementsTextCallOuts: {
+        type: String,
+        label: 'Auto position text call-outs for measurements when creating them.',
+        defaultValue: 'TRBL'
     }
 });
 
diff --git a/config/orthancDICOMWeb.json b/config/orthancDICOMWeb.json
index d112feea1..2f564a6ce 100644
--- a/config/orthancDICOMWeb.json
+++ b/config/orthancDICOMWeb.json
@@ -24,7 +24,8 @@
         "studyListFunctionsEnabled": true,
         "leftSidebarOpen": false,
         "displaySetNavigationLoopOverSeries": false,
-        "displaySetNavigationMultipleViewports": true
+        "displaySetNavigationMultipleViewports": true,
+        "autoPositionMeasurementsTextCallOuts": "TRLB"
     }
   }
 }