diff --git a/src/ds4.scss b/src/ds4.scss
index 212a180f..9ee0c00f 100644
--- a/src/ds4.scss
+++ b/src/ds4.scss
@@ -21,4 +21,5 @@
     @include meta.load-css("scss/components/tabs");
     @include meta.load-css("scss/components/talent_rank_equation");
     @include meta.load-css("scss/components/currency");
+    @include meta.load-css("scss/components/rollable_image");
 }
diff --git a/src/lang/de.json b/src/lang/de.json
index 31800739..3e2c0ae9 100644
--- a/src/lang/de.json
+++ b/src/lang/de.json
@@ -5,6 +5,9 @@
     "DS4.UserInteractionAddEffect": "Neuer Effekt",
     "DS4.UserInteractionEditEffect": "Effekt bearbeiten",
     "DS4.UserInteractionDeleteEffect": "Effekt löschen",
+    "DS4.EntityImageAltText": "Bild von {name}",
+    "DS4.RollableImageRollableTitle": "Für {name} würfeln",
+    "DS4.DiceOverlayImageAltText": "Bild eines W20",
     "DS4.NotOwned": "Nicht besessen",
     "DS4.HeadingBiography": "Biografie",
     "DS4.HeadingDetails": "Details",
@@ -15,8 +18,9 @@
     "DS4.HeadingSpells": "Zaubersprüche",
     "DS4.HeadingDescription": "Beschreibung",
     "DS4.HeadingSpecialCreatureAbilities": "Besondere Fähigkeiten",
-    "DS4.AttackType": "Angriffstyp",
-    "DS4.AttackTypeAbbr": "AT",
+    "DS4.AttackType": "Angriffsart",
+    "DS4.AttackTypeAbbr": "AA",
+    "DS4.AttackTypeSelection": "Welche Angriffsart?",
     "DS4.WeaponBonus": "Waffenbonus",
     "DS4.WeaponBonusAbbr": "WB",
     "DS4.OpponentDefense": "Gegnerabwehr",
@@ -184,6 +188,12 @@
     "DS4.ErrorDiceCritOverlap": "Es gibt eine Überlappung zwischen Patzern und Immersiegen.",
     "DS4.ErrorExplodingRecursionLimitExceeded": "Die maximale Rekursionstiefe für slayende Würfelwürfe wurde überschritten.",
     "DS4.ErrorDuringMigration": "Fehler während der Aktualisierung des DS4 Systems von Migrationsversion {currentVersion} auf {targetVersion}. Der Fehler trat während der Ausführung des Migrationsskripts mit der Version {migrationVersion} auf. Spätere Migrationsskripte wurden nicht ausgeführt. Mehr Details finden Sie in der Entwicklerkonsole (F12).",
+    "DS4.ErrorCannotRollUnownedItem": "Für das Item '{name}' ({id}) kann nicht gewürfelt werden, da es keinem Aktor gehört.",
+    "DS4.ErrorRollingForItemTypeNotPossible": "Würfeln ist für Items vom Typ '{type}' nicht möglich.",
+    "DS4.ErrorWrongItemType": "Ein Item vom Type '{expectedType}' wurde erwartet aber das Item '{name}' ({id}) ist vom Typ '{actualType}'.",
+    "DS4.ErrorUnexpectedAttackType": "Unerwartete Angriffsart '{actualType}', erwartete Angriffarten: {expectedTypes}",
+    "DS4.ErrorItemMustBeEquippedToBeRolled": "Um für das Item '{name}' ({id}) vom Typ '{type}' zu würfeln, muss es ausgerüstet sein.",
+    "DS4.InfoManuallyEnterSpellBonus": "Der korrekte Wert für den Zauberbonus '{spellBonus}' des Zaubers '{name}' musss manuell angegeben werden.",
     "DS4.InfoSystemUpdateStart": "Aktualisiere DS4 System von Migrationsversion {currentVersion} auf {targetVersion}. Bitte haben Sie etwas Geduld, schließen Sie nicht das Spiel und fahren Sie nicht den Server herunter.",
     "DS4.InfoSystemUpdateCompleted": "Aktualisierung des DS4 Systems von Migrationsversion {currentVersion} auf {targetVersion} erfolgreich!",
     "DS4.UnitRounds": "Runden",
@@ -200,9 +210,9 @@
     "DS4.UnitKilometersAbbr": "km",
     "DS4.UnitCustom": "individuell",
     "DS4.UnitCustomAbbr": " ",
+    "DS4.GenericOkButton": "OK",
+    "DS4.GenericCancelButton": "Abbrechen",
     "DS4.RollDialogDefaultTitle": "Proben-Optionen",
-    "DS4.RollDialogOkButton": "OK",
-    "DS4.RollDialogCancelButton": "Abbrechen",
     "DS4.ErrorUnexpectedHtmlType": "Typfehler: Erwartet wurde '{exType}', tatsächlich erhalten wurde '{realType}'.",
     "DS4.ErrorCouldNotFindForm": "Konnte HTML Element '{htmlElement}' nicht finden.",
     "DS4.ErrorActorDoesNotHaveItem": "Der Aktor '{actor}' hat kein Item mit der ID '{id}'.",
diff --git a/src/lang/en.json b/src/lang/en.json
index 0894350b..056091c6 100644
--- a/src/lang/en.json
+++ b/src/lang/en.json
@@ -5,6 +5,9 @@
     "DS4.UserInteractionAddEffect": "Add Effect",
     "DS4.UserInteractionEditEffect": "Edit Effect",
     "DS4.UserInteractionDeleteEffect": "Delete Effect",
+    "DS4.EntityImageAltText": "Image of {name}",
+    "DS4.RollableImageRollableTitle": "Roll for {name}",
+    "DS4.DiceOverlayImageAltText": "Image of a d20",
     "DS4.NotOwned": "No owner",
     "DS4.HeadingBiography": "Biography",
     "DS4.HeadingDetails": "Details",
@@ -17,6 +20,7 @@
     "DS4.HeadingSpecialCreatureAbilities": "Special Abilities",
     "DS4.AttackType": "Attack Type",
     "DS4.AttackTypeAbbr": "AT",
+    "DS4.AttackTypeSelection": "Which Attack Type?",
     "DS4.WeaponBonus": "Weapon Bonus",
     "DS4.WeaponBonusAbbr": "WB",
     "DS4.OpponentDefense": "Opponent Defense",
@@ -184,6 +188,12 @@
     "DS4.ErrorDiceCritOverlap": "There's an overlap between Fumbles and Coups",
     "DS4.ErrorExplodingRecursionLimitExceeded": "Maximum recursion depth for exploding dice roll exceeded",
     "DS4.ErrorDuringMigration": "Error while migrating DS4 system from migration version {currentVersion} to {targetVersion}. The error occurred during execution of migration script with version {migrationVersion}. Later migrations have not been executed. For more details, please look at the development console (F12).",
+    "DS4.ErrorCannotRollUnownedItem": "Rolling for item '{name}' ({id})is not possible because it is not owned.",
+    "DS4.ErrorRollingForItemTypeNotPossible": "Rolling is not possible for items of type '{type}'.",
+    "DS4.ErrorWrongItemType": "Expected an item of type '{expectedType}' but item '{name}' ({id}) is of type '{actualType}'.",
+    "DS4.ErrorUnexpectedAttackType": "Unexpected attack type '{actualType}', expected it to be one of: {expectedTypes}",
+    "DS4.ErrorItemMustBeEquippedToBeRolled": "To roll for item '{name}' ({id}) of type '{type}', it needs to be equipped.",
+    "DS4.InfoManuallyEnterSpellBonus": "The correct value of the spell bons '{spellBonus}' of the spell '{name}' needs to be entered by manually.",
     "DS4.InfoSystemUpdateStart": "Migrating DS4 system from migration version {currentVersion} to {targetVersion}. Please be patient and do not close your game or shut down your server.",
     "DS4.InfoSystemUpdateCompleted": "Migration of DS4 system from migration version {currentVersion} to {targetVersion} successful!",
     "DS4.UnitRounds": "Rounds",
@@ -200,9 +210,9 @@
     "DS4.UnitKilometersAbbr": "km",
     "DS4.UnitCustom": "Custom Unit",
     "DS4.UnitCustomAbbr": " ",
+    "DS4.GenericOkButton": "Ok",
+    "DS4.GenericCancelButton": "Cancel",
     "DS4.RollDialogDefaultTitle": "Roll Options",
-    "DS4.RollDialogOkButton": "Ok",
-    "DS4.RollDialogCancelButton": "Cancel",
     "DS4.ErrorUnexpectedHtmlType": "Type Error: Expected '{exType}' but got '{realType}'.",
     "DS4.ErrorCouldNotFindForm": "Could not find HTML element '{htmlElement}'.",
     "DS4.ErrorActorDoesNotHaveItem": "The actor '{actor}' does not have any item with the id '{id}'.",
diff --git a/src/module/actor/actor-data.ts b/src/module/actor/actor-data.ts
index 9f12ef3e..7fcb8398 100644
--- a/src/module/actor/actor-data.ts
+++ b/src/module/actor/actor-data.ts
@@ -17,6 +17,7 @@ interface DS4ActorDataDataBase {
     attributes: DS4ActorDataDataAttributes;
     traits: DS4ActorDataDataTraits;
     combatValues: DS4ActorDataDataCombatValues;
+    rolling: DS4ActorDataDataRolling;
 }
 
 interface DS4ActorDataDataAttributes {
@@ -45,6 +46,11 @@ interface DS4ActorDataDataCombatValues {
     targetedSpellcasting: ModifiableData<number>;
 }
 
+interface DS4ActorDataDataRolling {
+    maximumCoupResult?: number;
+    minimumFumbleResult?: number;
+}
+
 interface DS4CharacterDataData extends DS4ActorDataDataBase {
     baseInfo: DS4CharacterDataDataBaseInfo;
     progression: DS4CharacterDataDataProgression;
diff --git a/src/module/actor/actor.ts b/src/module/actor/actor.ts
index 305ca04e..0e4cbb0d 100644
--- a/src/module/actor/actor.ts
+++ b/src/module/actor/actor.ts
@@ -25,6 +25,11 @@ export class DS4Actor extends Actor<DS4ActorData, DS4Item> {
     prepareBaseData(): void {
         const data = this.data;
 
+        data.data.rolling = {
+            minimumFumbleResult: 20,
+            maximumCoupResult: 1,
+        };
+
         const attributes = data.data.attributes;
         Object.values(attributes).forEach(
             (attribute: ModifiableData<number>) => (attribute.total = attribute.base + attribute.mod),
diff --git a/src/module/actor/sheets/actor-sheet.ts b/src/module/actor/sheets/actor-sheet.ts
index aee139ff..e75f1be7 100644
--- a/src/module/actor/sheets/actor-sheet.ts
+++ b/src/module/actor/sheets/actor-sheet.ts
@@ -124,8 +124,7 @@ export class DS4ActorSheet extends ActorSheet<ActorSheet.Data<DS4Actor>> {
 
         html.find(".item-change").on("change", this._onItemChange.bind(this));
 
-        // Rollable abilities.
-        html.find(".rollable").click(this._onRoll.bind(this));
+        html.find(".rollable-item").on("click", this._onRoll.bind(this));
     }
 
     /**
@@ -239,17 +238,9 @@ export class DS4ActorSheet extends ActorSheet<ActorSheet.Data<DS4Actor>> {
      */
     protected _onRoll(event: JQuery.ClickEvent): void {
         event.preventDefault();
-        const element = event.currentTarget;
-        const dataset = element.dataset;
-
-        if (dataset.roll) {
-            const roll = new Roll(dataset.roll, this.actor.data.data);
-            const label = dataset.label ? `Rolling ${dataset.label}` : "";
-            roll.roll().toMessage({
-                speaker: ChatMessage.getSpeaker({ actor: this.actor }),
-                flavor: label,
-            });
-        }
+        const id = $(event.currentTarget).parents(".item").data("itemId");
+        const item = this.actor.getOwnedItem(id);
+        item.roll();
     }
 
     /** @override */
diff --git a/src/module/ds4.ts b/src/module/ds4.ts
index c8243f4e..67d03724 100644
--- a/src/module/ds4.ts
+++ b/src/module/ds4.ts
@@ -8,7 +8,8 @@ import { DS4CreatureActorSheet } from "./actor/sheets/creature-sheet";
 import { createCheckRoll } from "./rolls/check-factory";
 import { registerSystemSettings } from "./settings";
 import { migration } from "./migrations";
-import handlebarsHelpers from "./handlebars-helpers";
+import registerHandlebarsHelpers from "./handlebars/handlebars-helpers";
+import registerHandlebarsPartials from "./handlebars/handlebars-partials";
 
 Hooks.once("init", async () => {
     console.log(`DS4 | Initializing the DS4 Game System\n${DS4.ASCII}`);
@@ -44,37 +45,6 @@ Hooks.once("init", async () => {
     registerHandlebarsHelpers();
 });
 
-async function registerHandlebarsPartials() {
-    const templatePaths = [
-        "systems/ds4/templates/item/partials/sheet-header.hbs",
-        "systems/ds4/templates/item/partials/description.hbs",
-        "systems/ds4/templates/item/partials/details.hbs",
-        "systems/ds4/templates/item/partials/effects.hbs",
-        "systems/ds4/templates/item/partials/body.hbs",
-        "systems/ds4/templates/actor/partials/items-overview.hbs",
-        "systems/ds4/templates/actor/partials/talents-abilities-overview.hbs",
-        "systems/ds4/templates/actor/partials/spells-overview.hbs",
-        "systems/ds4/templates/actor/partials/overview-add-button.hbs",
-        "systems/ds4/templates/actor/partials/overview-control-buttons.hbs",
-        "systems/ds4/templates/actor/partials/attributes-traits.hbs",
-        "systems/ds4/templates/actor/partials/combat-values.hbs",
-        "systems/ds4/templates/actor/partials/profile.hbs",
-        "systems/ds4/templates/actor/partials/character-progression.hbs",
-        "systems/ds4/templates/actor/partials/special-creature-abilities-overview.hbs",
-        "systems/ds4/templates/actor/partials/character-inventory.hbs",
-        "systems/ds4/templates/actor/partials/creature-inventory.hbs",
-        "systems/ds4/templates/actor/partials/talent-rank-equation.hbs",
-        "systems/ds4/templates/actor/partials/item-list-header.hbs",
-        "systems/ds4/templates/actor/partials/item-list-entry.hbs",
-        "systems/ds4/templates/actor/partials/currency.hbs",
-    ];
-    return loadTemplates(templatePaths);
-}
-
-function registerHandlebarsHelpers() {
-    Object.entries(handlebarsHelpers).forEach(([key, helper]) => Handlebars.registerHelper(key, helper));
-}
-
 /**
  * This function runs after game data has been requested and loaded from the servers, so entities exist
  */
diff --git a/src/module/handlebars-helpers.ts b/src/module/handlebars-helpers.ts
deleted file mode 100644
index 95144da3..00000000
--- a/src/module/handlebars-helpers.ts
+++ /dev/null
@@ -1,10 +0,0 @@
-export default { htmlToPlainText, isEmpty };
-
-function htmlToPlainText(input: string | null | undefined): string | null | undefined {
-    if (!input) return;
-    return $(input).text();
-}
-
-function isEmpty(input: Array<unknown> | null | undefined): boolean {
-    return (input?.length ?? 0) === 0;
-}
diff --git a/src/module/handlebars/handlebars-helpers.ts b/src/module/handlebars/handlebars-helpers.ts
new file mode 100644
index 00000000..fef92681
--- /dev/null
+++ b/src/module/handlebars/handlebars-helpers.ts
@@ -0,0 +1,12 @@
+export default function registerHandlebarsHelpers(): void {
+    Object.entries(helpers).forEach(([key, helper]) => Handlebars.registerHelper(key, helper));
+}
+
+const helpers = {
+    htmlToPlainText: (input: string | null | undefined): string | null | undefined => {
+        if (!input) return;
+        return $(input).text();
+    },
+
+    isEmpty: (input: Array<unknown> | null | undefined): boolean => (input?.length ?? 0) === 0,
+};
diff --git a/src/module/handlebars/handlebars-partials.ts b/src/module/handlebars/handlebars-partials.ts
new file mode 100644
index 00000000..81945ebc
--- /dev/null
+++ b/src/module/handlebars/handlebars-partials.ts
@@ -0,0 +1,27 @@
+export default async function registerHandlebarsPartials(): Promise<void> {
+    const templatePaths = [
+        "systems/ds4/templates/item/partials/sheet-header.hbs",
+        "systems/ds4/templates/item/partials/description.hbs",
+        "systems/ds4/templates/item/partials/details.hbs",
+        "systems/ds4/templates/item/partials/effects.hbs",
+        "systems/ds4/templates/item/partials/body.hbs",
+        "systems/ds4/templates/actor/partials/items-overview.hbs",
+        "systems/ds4/templates/actor/partials/talents-abilities-overview.hbs",
+        "systems/ds4/templates/actor/partials/spells-overview.hbs",
+        "systems/ds4/templates/actor/partials/overview-add-button.hbs",
+        "systems/ds4/templates/actor/partials/overview-control-buttons.hbs",
+        "systems/ds4/templates/actor/partials/attributes-traits.hbs",
+        "systems/ds4/templates/actor/partials/combat-values.hbs",
+        "systems/ds4/templates/actor/partials/profile.hbs",
+        "systems/ds4/templates/actor/partials/character-progression.hbs",
+        "systems/ds4/templates/actor/partials/special-creature-abilities-overview.hbs",
+        "systems/ds4/templates/actor/partials/character-inventory.hbs",
+        "systems/ds4/templates/actor/partials/creature-inventory.hbs",
+        "systems/ds4/templates/actor/partials/talent-rank-equation.hbs",
+        "systems/ds4/templates/actor/partials/item-list-header.hbs",
+        "systems/ds4/templates/actor/partials/item-list-entry.hbs",
+        "systems/ds4/templates/actor/partials/currency.hbs",
+        "systems/ds4/templates/common/partials/rollable-image.hbs",
+    ];
+    await loadTemplates(templatePaths);
+}
diff --git a/src/module/item/item-data.ts b/src/module/item/item-data.ts
index 5afd83b3..c28fbe86 100644
--- a/src/module/item/item-data.ts
+++ b/src/module/item/item-data.ts
@@ -32,8 +32,14 @@ type DS4LanguageData = DS4ItemDataHelper<DS4LanguageDataData, "language">;
 type DS4AlphabetData = DS4ItemDataHelper<DS4AlphabetDataData, "alphabet">;
 type DS4SpecialCreatureAbilityData = DS4ItemDataHelper<DS4SpecialCreatureAbilityDataData, "specialCreatureAbility">;
 
-interface DS4WeaponDataData extends DS4ItemDataDataBase, DS4ItemDataDataPhysical, DS4ItemDataDataEquipable {
-    attackType: "melee" | "ranged" | "meleeRanged";
+export type AttackType = keyof typeof DS4["i18n"]["attackTypes"];
+
+interface DS4WeaponDataData
+    extends DS4ItemDataDataBase,
+        DS4ItemDataDataPhysical,
+        DS4ItemDataDataEquipable,
+        DS4ItemDataDataRollable {
+    attackType: AttackType;
     weaponBonus: number;
     opponentDefense: number;
 }
@@ -55,7 +61,7 @@ interface DS4TalentRank extends ModifiableData<number> {
     max: number;
 }
 
-interface DS4SpellDataData extends DS4ItemDataDataBase, DS4ItemDataDataEquipable {
+interface DS4SpellDataData extends DS4ItemDataDataBase, DS4ItemDataDataEquipable, DS4ItemDataDataRollable {
     spellType: "spellcasting" | "targetedSpellcasting";
     bonus: string;
     spellCategory:
@@ -109,6 +115,10 @@ interface DS4ItemDataDataEquipable {
     equipped: boolean;
 }
 
+interface DS4ItemDataDataRollable {
+    rollable?: boolean;
+}
+
 interface DS4ItemDataDataProtective {
     armorValue: number;
 }
diff --git a/src/module/item/item.ts b/src/module/item/item.ts
index 5c0a9f3d..ac9b90cd 100644
--- a/src/module/item/item.ts
+++ b/src/module/item/item.ts
@@ -1,4 +1,8 @@
-import { DS4ItemData } from "./item-data";
+import { DS4Actor } from "../actor/actor";
+import { DS4 } from "../config";
+import { createCheckRoll } from "../rolls/check-factory";
+import notifications from "../ui/notifications";
+import { AttackType, DS4ItemData } from "./item-data";
 
 /**
  * The Item class for DS4
@@ -17,6 +21,9 @@ export class DS4Item extends Item<DS4ItemData> {
             const data = this.data.data;
             data.rank.total = data.rank.base + data.rank.mod;
         }
+        if (this.data.type === "weapon" || this.data.type === "spell") {
+            this.data.data.rollable = this.data.data.equipped;
+        }
     }
 
     isNonEquippedEuipable(): boolean {
@@ -32,4 +39,138 @@ export class DS4Item extends Item<DS4ItemData> {
         }
         return 1;
     }
+
+    /**
+     * Roll a check for a action with this item.
+     */
+    async roll(): Promise<void> {
+        if (!this.isOwnedItem()) {
+            throw new Error(game.i18n.format("DS4.ErrorCannotRollUnownedItem", { name: this.name, id: this.id }));
+        }
+
+        switch (this.data.type) {
+            case "weapon":
+                return this.rollWeapon();
+            case "spell":
+                return this.rollSpell();
+            default:
+                throw new Error(game.i18n.format("DS4.ErrorRollingForItemTypeNotPossible", { type: this.data.type }));
+        }
+    }
+
+    protected async rollWeapon(this: this & { readonly isOwned: true }): Promise<void> {
+        if (!(this.data.type === "weapon")) {
+            throw new Error(
+                game.i18n.format("DS4.ErrorWrongItemType", {
+                    actualType: this.data.type,
+                    expectedType: "weapon",
+                    id: this.id,
+                    name: this.name,
+                }),
+            );
+        }
+
+        if (!this.data.data.equipped) {
+            throw new Error(
+                game.i18n.format("DS4.ErrorItemMustBeEquippedToBeRolled", {
+                    name: this.name,
+                    id: this.id,
+                    type: this.data.type,
+                }),
+            );
+        }
+
+        const ownerDataData = ((this.actor as unknown) as DS4Actor).data.data; // TODO(types): Improve so that the concrete Actor type is known here
+        const weaponBonus = this.data.data.weaponBonus;
+        const combatValue = await this.getCombatValueKeyForAttackType(this.data.data.attackType);
+        const checkTargetValue = (ownerDataData.combatValues[combatValue].total as number) + weaponBonus;
+        await createCheckRoll(checkTargetValue, {
+            rollMode: game.settings.get("core", "rollMode"),
+            maxCritSuccess: ownerDataData.rolling.maximumCoupResult,
+            minCritFailure: ownerDataData.rolling.minimumFumbleResult,
+        });
+    }
+
+    protected async rollSpell(): Promise<void> {
+        if (!(this.data.type === "spell")) {
+            throw new Error(
+                game.i18n.format("DS4.ErrorWrongItemType", {
+                    actualType: this.data.type,
+                    expectedType: "spell",
+                    id: this.id,
+                    name: this.name,
+                }),
+            );
+        }
+
+        if (!this.data.data.equipped) {
+            throw new Error(
+                game.i18n.format("DS4.ErrorItemMustBeEquippedToBeRolled", {
+                    name: this.name,
+                    id: this.id,
+                    type: this.data.type,
+                }),
+            );
+        }
+
+        const ownerDataData = ((this.actor as unknown) as DS4Actor).data.data; // TODO(types): Improve so that the concrete Actor type is known here
+        const spellBonus = Number.isNumeric(this.data.data.bonus) ? parseInt(this.data.data.bonus) : undefined;
+        if (spellBonus === undefined) {
+            notifications.info(
+                game.i18n.format("DS4.InfoManuallyEnterSpellBonus", {
+                    name: this.name,
+                    spellBonus: this.data.data.bonus,
+                }),
+            );
+        }
+        const spellType = this.data.data.spellType;
+        const checkTargetValue = (ownerDataData.combatValues[spellType].total as number) + (spellBonus ?? 0);
+
+        await createCheckRoll(checkTargetValue, {
+            rollMode: game.settings.get("core", "rollMode"),
+            maxCritSuccess: ownerDataData.rolling.maximumCoupResult,
+            minCritFailure: ownerDataData.rolling.minimumFumbleResult,
+        });
+    }
+
+    protected async getCombatValueKeyForAttackType(attackType: AttackType): Promise<"meleeAttack" | "rangedAttack"> {
+        if (attackType === "meleeRanged") {
+            const { melee, ranged } = { ...DS4.i18n.attackTypes };
+            const identifier = "attack-type-selection";
+            const label = game.i18n.localize("DS4.AttackType");
+            const answer = Dialog.prompt({
+                title: game.i18n.localize("DS4.AttackTypeSelection"),
+                content: await renderTemplate("systems/ds4/templates/common/simple-select-form.hbs", {
+                    label,
+                    identifier,
+                    options: { melee, ranged },
+                }),
+                label: game.i18n.localize("DS4.GenericOkButton"),
+                callback: (html) => {
+                    const selectedAttackType = html.find(`#${identifier}`).val();
+                    if (selectedAttackType !== "melee" && selectedAttackType !== "ranged") {
+                        throw new Error(
+                            game.i18n.format("DS4.ErrorUnexpectedAttackType", {
+                                actualType: selectedAttackType,
+                                expectedTypes: "'melee', 'ranged'",
+                            }),
+                        );
+                    }
+                    return `${selectedAttackType}Attack` as const;
+                },
+                render: () => undefined, // TODO(types): This is actually optional, remove when types are updated )
+                options: { jQuery: true },
+            });
+            return answer;
+        } else {
+            return `${attackType}Attack` as const;
+        }
+    }
+
+    /**
+     * Type-guarding variant to check if the item is owned.
+     */
+    isOwnedItem(): this is this & { readonly isOwned: true } {
+        return this.isOwned;
+    }
 }
diff --git a/src/module/rolls/check-factory.ts b/src/module/rolls/check-factory.ts
index eb68789d..2b3556b7 100644
--- a/src/module/rolls/check-factory.ts
+++ b/src/module/rolls/check-factory.ts
@@ -138,7 +138,7 @@ async function askGmModifier(
                 buttons: {
                     ok: {
                         icon: '<i class="fas fa-check"></i>',
-                        label: game.i18n.localize("DS4.RollDialogOkButton"),
+                        label: game.i18n.localize("DS4.GenericOkButton"),
                         callback: (html) => {
                             if (!("jquery" in html)) {
                                 throw new Error(
@@ -160,7 +160,7 @@ async function askGmModifier(
                     },
                     cancel: {
                         icon: '<i class="fas fa-times"></i>',
-                        label: game.i18n.localize("DS4.RollDialogCancelButton"),
+                        label: game.i18n.localize("DS4.GenericCancelButton"),
                     },
                 },
                 default: "ok",
diff --git a/src/scss/components/_item_list.scss b/src/scss/components/_item_list.scss
index afebd6cc..dfa69c5c 100644
--- a/src/scss/components/_item_list.scss
+++ b/src/scss/components/_item_list.scss
@@ -15,31 +15,31 @@
     padding: 0;
 
     &--weapon {
-        grid-template-columns: $row-height $row-height 3ch 3fr $row-height 1fr 3ch 5fr 4ch;
+        grid-template-columns: $row-height $row-height 3ch 3fr $row-height 1fr 3ch 5fr 5ch;
     }
     &--armor {
-        grid-template-columns: $row-height $row-height 3ch 3fr 1fr 1fr 3ch 5fr 4ch;
+        grid-template-columns: $row-height $row-height 3ch 3fr 1fr 1fr 3ch 5fr 5ch;
     }
     &--shield {
-        grid-template-columns: $row-height $row-height 3ch 1fr 3ch 3fr 4ch;
+        grid-template-columns: $row-height $row-height 3ch 1fr 3ch 3fr 5ch;
     }
     &--equipment {
-        grid-template-columns: $row-height $row-height 3ch 1fr 10ch 3fr 4ch;
+        grid-template-columns: $row-height $row-height 3ch 1fr 10ch 3fr 5ch;
     }
     &--loot {
-        grid-template-columns: $row-height 3ch 1fr 10ch 3fr 4ch;
+        grid-template-columns: $row-height 3ch 1fr 10ch 3fr 5ch;
     }
     &--spell {
-        grid-template-columns: $row-height $row-height 2fr $row-height 1fr 1fr 1fr 1fr 4ch;
+        grid-template-columns: $row-height $row-height 2fr $row-height 1fr 1fr 1fr 1fr 5ch;
     }
     &--talent {
-        grid-template-columns: $row-height 1fr 1fr 3fr 4ch;
+        grid-template-columns: $row-height 1fr 21ch 3fr 5ch;
     }
     &--racial-ability,
     &--language,
     &--alphabet,
     &--special-creature-ability {
-        grid-template-columns: $row-height 1fr 3fr 4ch;
+        grid-template-columns: $row-height 1fr 3fr 5ch;
     }
 
     &__row {
@@ -53,13 +53,12 @@
             height: $row-height;
             line-height: $row-height;
             white-space: nowrap;
+            overflow-y: hidden;
         }
     }
 
     &__image {
-        background-position: center;
-        background-repeat: no-repeat;
-        background-size: 100%;
+        border: none;
     }
 
     &__editable {
@@ -89,6 +88,14 @@
             text-overflow: ellipsis;
         }
     }
+
+    &__control-buttons {
+        display: grid;
+        grid-template-columns: 1fr 1fr;
+        text-align: center;
+        width: 100%;
+        padding: 0 calc(1em / 3);
+    }
 }
 
 .ds4-item-list-title {
diff --git a/src/scss/components/_rollable_image.scss b/src/scss/components/_rollable_image.scss
new file mode 100644
index 00000000..ba33bca7
--- /dev/null
+++ b/src/scss/components/_rollable_image.scss
@@ -0,0 +1,33 @@
+.ds4-rollable-image {
+    position: relative;
+
+    &--rollable {
+        cursor: pointer;
+
+        &:hover {
+            .ds4-rollable-image__image {
+                opacity: 0.25;
+            }
+
+            .ds4-rollable-image__overlay {
+                opacity: 1;
+            }
+        }
+    }
+
+    &__image {
+        border: none;
+        transition: 0.1s ease;
+    }
+
+    &__overlay {
+        border: none;
+        bottom: 0;
+        left: 0;
+        opacity: 0;
+        position: absolute;
+        right: 0;
+        top: 0;
+        transition: 0.1s ease;
+    }
+}
diff --git a/src/templates/actor/partials/item-list-entry.hbs b/src/templates/actor/partials/item-list-entry.hbs
index f74093b6..ca08d0fc 100644
--- a/src/templates/actor/partials/item-list-entry.hbs
+++ b/src/templates/actor/partials/item-list-entry.hbs
@@ -17,7 +17,9 @@
     {{/if}}
 
     {{!-- image --}}
-    <div class="ds4-item-list__image" style="background-image: url('{{itemData.img}}')" title="{{itemData.name}}"></div>
+    {{> systems/ds4/templates/common/partials/rollable-image.hbs rollable=itemData.data.rollable src=itemData.img
+    alt=(localize "DS4.EntityImageAltText" name=itemData.name) title=itemData.name rollableTitle=(localize
+    "DS4.RollableImageRollableTitle" name=itemData.name) rollableClass="rollable-item"}}
 
     {{!-- amount --}}
     {{#if hasQuantity}}
@@ -41,5 +43,5 @@
     {{/unless}}
 
     {{!-- control buttons --}}
-    {{> systems/ds4/templates/actor/partials/overview-control-buttons.hbs }}
+    {{> systems/ds4/templates/actor/partials/overview-control-buttons.hbs class="ds4-item-list__control-buttons" }}
 </li>
diff --git a/src/templates/actor/partials/items-overview.hbs b/src/templates/actor/partials/items-overview.hbs
index c3544805..094109b1 100644
--- a/src/templates/actor/partials/items-overview.hbs
+++ b/src/templates/actor/partials/items-overview.hbs
@@ -20,10 +20,8 @@
     {{#each itemsByType.weapon as |itemData id|}}
     {{#> systems/ds4/templates/actor/partials/item-list-entry.hbs itemData=itemData isEquipable=true hasQuantity=true}}
     {{!-- attack type --}}
-    <div class="ds4-item-list__image"
-        style="background-image: url('{{lookup ../../config.icons.attackTypes  itemData.data.attackType}}')"
-        title="{{lookup ../../config.i18n.attackTypes  itemData.data.attackType}}">
-    </div>
+    <img class="ds4-item-list__image" src="{{lookup ../../config.icons.attackTypes itemData.data.attackType}}"
+        title="{{lookup ../../config.i18n.attackTypes itemData.data.attackType}}" />
 
     {{!-- weapon bonus --}}
     <div>{{ itemData.data.weaponBonus}}</div>
diff --git a/src/templates/actor/partials/overview-control-buttons.hbs b/src/templates/actor/partials/overview-control-buttons.hbs
index 2c85899f..ac7177b2 100644
--- a/src/templates/actor/partials/overview-control-buttons.hbs
+++ b/src/templates/actor/partials/overview-control-buttons.hbs
@@ -1,8 +1,10 @@
 {{!--
 !-- Render a group of an "edit" and a "delete" button for the current item.
 !-- The current item is defined by the data-item-id HTML property of the parent li element.
+!-- @param class: Additional CSS class(es) for the controls
 --}}
-<div class="item-controls">
+<div class="item-controls {{class}}">
     <a class="item-control item-edit" title="{{localize 'DS4.UserInteractionEditItem'}}"><i class="fas fa-edit"></i></a>
-    <a class="item-control item-delete" title="{{localize 'DS4.UserInteractionDeleteItem'}}"><i class="fas fa-trash"></i></a>
+    <a class="item-control item-delete" title="{{localize 'DS4.UserInteractionDeleteItem'}}"><i
+            class="fas fa-trash"></i></a>
 </div>
diff --git a/src/templates/actor/partials/spells-overview.hbs b/src/templates/actor/partials/spells-overview.hbs
index e9861c77..e5f9b008 100644
--- a/src/templates/actor/partials/spells-overview.hbs
+++ b/src/templates/actor/partials/spells-overview.hbs
@@ -60,10 +60,8 @@ titleKey=titleKey}}
         {{#> systems/ds4/templates/actor/partials/item-list-entry.hbs itemData=itemData isEquipable=true
         hideDescription=true}}
         {{!-- spell type --}}
-        <div class="ds4-item-list__image"
-            style="background-image: url('{{lookup ../../config.icons.spellTypes itemData.data.spellType}}')"
-            title="{{lookup ../../config.i18n.spellTypes itemData.data.spellType}}">
-        </div>
+        <img class="ds4-item-list__image" src="{{lookup ../../config.icons.spellTypes itemData.data.spellType}}"
+            title="{{lookup ../../config.i18n.spellTypes itemData.data.spellType}}" />
 
         {{!-- spell bonus --}}
         <input class="ds4-item-list__editable item-change" type="text" data-dtype="String" data-property="data.bonus"
diff --git a/src/templates/common/partials/rollable-image.hbs b/src/templates/common/partials/rollable-image.hbs
new file mode 100644
index 00000000..08abc7d1
--- /dev/null
+++ b/src/templates/common/partials/rollable-image.hbs
@@ -0,0 +1,17 @@
+{{!--
+!-- Render an image that has a dice overlay image.
+!-- @param rollable: A flag indicating whether or not the image is actually rollable.
+!-- @param rollableClass: The CSS class(es) to add if the image is rollable.
+!-- @param title: The title for the rollable image if it is not actually rollable.
+!-- @param rollableTitle: The title for the rollable image if it is rollable.
+!-- @param src: The path to the image.
+!-- @param alt: An alternate text for the image.
+--}}
+<div class="ds4-rollable-image{{#if rollable}} ds4-rollable-image--rollable {{rollableClass}}{{/if}}"
+    title="{{#if rollable}}{{rollableTitle}}{{else}}{{title}}{{/if}}">
+    <img class="ds4-rollable-image__image" alt="{{alt}}" src="{{src}}" />
+    {{#if rollable}}
+    <img class="ds4-rollable-image__overlay" alt="{{localize 'DS4.DiceOverlayImageAltText'}}"
+        src="icons/svg/d20-black.svg" />
+    {{/if}}
+</div>
diff --git a/src/templates/common/simple-select-form.hbs b/src/templates/common/simple-select-form.hbs
new file mode 100644
index 00000000..dc82f319
--- /dev/null
+++ b/src/templates/common/simple-select-form.hbs
@@ -0,0 +1,19 @@
+{{!--
+!-- Render a simple form with a single select element. It uses the default form classes of Foundry VTT.
+!-- @param identifier: The identifier to use as id for the select element. Can be used to query the value later on.
+!-- @param label: Text to display as the label for the select element.
+!-- @param options: Key-value pairs that describe the options. The keys are used for the value attribute of the
+options, the values are used as content.
+--}}
+<form class="ds4-simple-form">
+    <div class="form-group">
+        <label for="{{identifier}}">{{label}}</label>
+        <div class="form-fields">
+            <select name="{{identifier}}" id="{{identifier}}">
+                {{#each options as | value key |}}
+                <option value="{{key}}">{{value}}</option>
+                {{/each}}
+            </select>
+        </div>
+    </div>
+</form>