diff --git a/lang/en.json b/lang/en.json
index e358977f..0186ae3e 100755
--- a/lang/en.json
+++ b/lang/en.json
@@ -2405,6 +2405,14 @@
                     "hideAttribution": {
                         "label": "Hide Attribution"
                     },
+                    "showTokenDistance": {
+                        "label": "Show Token Distance on Hover",
+                        "choices": {
+                            "always": "Always",
+                            "encounters": "Encounters",
+                            "never": "Never"
+                        }
+                    },
                     "expandedTitle": "Auto-expand Descriptions",
                     "extendCharacterDescriptions": {
                         "label": "Characters"
diff --git a/module/canvas/placeables/measuredTemplate.mjs b/module/canvas/placeables/measuredTemplate.mjs
index ef7d284b..e1ea79f5 100644
--- a/module/canvas/placeables/measuredTemplate.mjs
+++ b/module/canvas/placeables/measuredTemplate.mjs
@@ -18,8 +18,9 @@ export default class DhMeasuredTemplate extends foundry.canvas.placeables.Measur
 
     static getRangeLabels(distanceValue, settings) {
         let result = { distance: distanceValue, units: '' };
-        const sceneRangeMeasurement = canvas.scene.flags.daggerheart?.rangeMeasurement;
+        if (!settings.enabled) return result;
 
+        const sceneRangeMeasurement = canvas.scene.flags.daggerheart?.rangeMeasurement;
         const { disable, custom } = CONFIG.DH.GENERAL.sceneRangeMeasurementSetting;
         if (sceneRangeMeasurement?.setting === disable.id) {
             result.distance = distanceValue;
@@ -27,31 +28,9 @@ export default class DhMeasuredTemplate extends foundry.canvas.placeables.Measur
             return result;
         }
 
-        const melee = sceneRangeMeasurement?.setting === custom.id ? sceneRangeMeasurement.melee : settings.melee;
-        const veryClose =
-            sceneRangeMeasurement?.setting === custom.id ? sceneRangeMeasurement.veryClose : settings.veryClose;
-        const close = sceneRangeMeasurement?.setting === custom.id ? sceneRangeMeasurement.close : settings.close;
-        const far = sceneRangeMeasurement?.setting === custom.id ? sceneRangeMeasurement.far : settings.far;
-        if (distanceValue <= melee) {
-            result.distance = game.i18n.localize('DAGGERHEART.CONFIG.Range.melee.name');
-            return result;
-        }
-        if (distanceValue <= veryClose) {
-            result.distance = game.i18n.localize('DAGGERHEART.CONFIG.Range.veryClose.name');
-            return result;
-        }
-        if (distanceValue <= close) {
-            result.distance = game.i18n.localize('DAGGERHEART.CONFIG.Range.close.name');
-            return result;
-        }
-        if (distanceValue <= far) {
-            result.distance = game.i18n.localize('DAGGERHEART.CONFIG.Range.far.name');
-            return result;
-        }
-        if (distanceValue > far) {
-            result.distance = game.i18n.localize('DAGGERHEART.CONFIG.Range.veryFar.name');
-        }
-
+        const ranges = sceneRangeMeasurement?.setting === custom.id ? sceneRangeMeasurement : settings;
+        const distanceKey = ['melee', 'veryClose', 'close', 'far'].find(r => ranges[r] >= distanceValue);
+        result.distance = game.i18n.localize(`DAGGERHEART.CONFIG.Range.${distanceKey ?? 'veryFar'}.name`);
         return result;
     }
 }
diff --git a/module/canvas/placeables/token.mjs b/module/canvas/placeables/token.mjs
index 2266d0da..bc5c2a01 100644
--- a/module/canvas/placeables/token.mjs
+++ b/module/canvas/placeables/token.mjs
@@ -1,3 +1,5 @@
+import DhMeasuredTemplate from "./measuredTemplate.mjs";
+
 export default class DhTokenPlaceable extends foundry.canvas.placeables.Token {
     /** @inheritdoc */
     async _draw(options) {
@@ -78,6 +80,60 @@ export default class DhTokenPlaceable extends foundry.canvas.placeables.Token {
         return canvas.grid.measurePath([adjustedOriginPoint, adjustDestinationPoint]).distance;
     }
 
+    _onHoverIn(event, options) {
+        super._onHoverIn(event, options);
+
+        // Check if the setting is enabled
+        const setting = game.settings.get(CONFIG.DH.id, CONFIG.DH.SETTINGS.gameSettings.appearance).showTokenDistance;
+        if (setting === "never" || (setting === "encounters" && !game.combat?.started)) return;
+
+        // Check if this token isn't invisible and is actually being hovered
+        const isTokenValid =
+            this.visible &&
+            this.hover &&
+            !this.isPreview &&
+            !this.document.isSecret &&
+            !this.controlled &&
+            !this.animation;
+        if (!isTokenValid) return;
+
+        // Ensure we have a single controlled token
+        const originToken = canvas.tokens.controlled[0];
+        if (!originToken || canvas.tokens.controlled.length > 1) return;
+
+        // Determine the actual range
+        const ranges = game.settings.get(CONFIG.DH.id, CONFIG.DH.SETTINGS.gameSettings.variantRules).rangeMeasurement;
+        const distanceNum = originToken.distanceTo(this);
+        const distanceResult = DhMeasuredTemplate.getRangeLabels(distanceNum, ranges);
+        const distanceLabel = `${distanceResult.distance} ${distanceResult.units}`.trim();
+
+        // Create the element
+        const element = document.createElement('div');
+        element.id = 'token-hover-distance';
+        element.classList.add('waypoint-label', 'last');
+        const ruler = document.createElement('i');
+        ruler.classList.add('fa-solid', 'fa-ruler');
+        element.appendChild(ruler);
+        const labelEl = document.createElement('span');
+        labelEl.classList.add('total-measurement');
+        labelEl.textContent = distanceLabel;
+        element.appendChild(labelEl);
+
+        // Position the element and add to the DOM
+        const center = this.getCenterPoint();
+        element.style.setProperty('--transformY', 'calc(-100% - 10px)');
+        element.style.setProperty('--position-y', `${this.y}px`);
+        element.style.setProperty('--position-x', `${center.x}px`);
+        element.style.setProperty('--ui-scale', String(canvas.dimensions.uiScale));
+        document.querySelector('#token-hover-distance')?.remove();
+        document.querySelector('#measurement').appendChild(element);
+    }
+
+    _onHoverOut(...args) {
+        super._onHoverOut(...args);
+        document.querySelector('#token-hover-distance')?.remove();
+    }
+
     /** Returns the point at which a line starting at origin and ending at destination intersects the edge of the bounds */
     #getEdgeBoundary(bounds, originPoint, destinationPoint) {
         const points = [
diff --git a/module/data/settings/Appearance.mjs b/module/data/settings/Appearance.mjs
index 2b8d3b27..d7a638d7 100644
--- a/module/data/settings/Appearance.mjs
+++ b/module/data/settings/Appearance.mjs
@@ -42,6 +42,25 @@ export default class DhAppearance extends foundry.abstract.DataModel {
                 damage: new BooleanField(),
                 target: new BooleanField()
             }),
+            showTokenDistance: new StringField({
+                required: true,
+                choices: {
+                    always: {
+                        value: 'always',
+                        label: 'DAGGERHEART.SETTINGS.Appearance.FIELDS.showTokenDistance.choices.always'
+                    },
+                    encounters: {
+                        value: 'encounters',
+                        label: 'DAGGERHEART.SETTINGS.Appearance.FIELDS.showTokenDistance.choices.encounters'
+                    },
+                    never: {
+                        value: 'never',
+                        label: 'DAGGERHEART.SETTINGS.Appearance.FIELDS.showTokenDistance.choices.never'
+                    }
+                },
+                nullable: false,
+                initial: 'always'
+            }),
             hideAttribution: new BooleanField(),
             showGenericStatusEffects: new BooleanField({ initial: true })
         };
diff --git a/templates/settings/appearance-settings/main.hbs b/templates/settings/appearance-settings/main.hbs
index 75a7e634..32dd9e63 100644
--- a/templates/settings/appearance-settings/main.hbs
+++ b/templates/settings/appearance-settings/main.hbs
@@ -16,6 +16,10 @@
     value=setting.showGenericStatusEffects
     localize=true}}
     {{formGroup
+    fields.showTokenDistance
+    value=setting.showTokenDistance
+    localize=true}}
+    {{formGroup
     fields.hideAttribution
     value=setting.hideAttribution
     localize=true}}