diff --git a/lang/en.json b/lang/en.json
index 6bf4459..44be259 100644
--- a/lang/en.json
+++ b/lang/en.json
@@ -22,6 +22,8 @@
   "AWEMMY.Condition.Edge": "Edge",
   "AWEMMY.Condition.Hampered": "Hampered",
   "AWEMMY.Condition.Inhibited": "Inhibited",
+  "AWEMMY.Condition.Penalty": "Penalty",
+  "AWEMMY.Condition.DCPenalty": "DC Penalty",
   "AWEMMY.Condition.Jumbled": "Jumbled",
   "AWEMMY.Condition.Mishap": "Mishap",
   "AWEMMY.Condition.Prone": "Prone",
@@ -31,6 +33,7 @@
   "AWEMMY.Condition.Panel": "Conditions",
   "AWEMMY.Roll.ConditionBonus": "Condition",
   "AWEMMY.Item.Description": "Description",
+  "AWEMMY.Item.RollBonus": "Roll Bonus",
   "AWEMMY.Error.TraitPasteFailed": "Failed to update traits — please try again.",
   "AWEMMY.Kit.Use": "Use Kit",
   "AWEMMY.Kit.Used": "{name} used",
@@ -59,9 +62,13 @@
   "AWEMMY.Roll.Check": "Check",
   "AWEMMY.Roll.Roll": "Roll",
   "AWEMMY.Roll.DialogTitle": "Roll: {name}",
-  "AWEMMY.Roll.SituationalBonus": "Situational Bonus",
+  "AWEMMY.Roll.RollTwice": "Roll Twice",
+  "AWEMMY.Roll.Normal": "Normal",
+  "AWEMMY.Roll.TakeHigher": "Take Higher",
+  "AWEMMY.Roll.TakeLower": "Take Lower",
+  "AWEMMY.Roll.SituationalBonus": "Bonus or Penalty",
   "AWEMMY.Roll.AttributeBonus": "Attribute Bonus",
-  "AWEMMY.Roll.KnowledgeBonus": "Knowledge Bonus",
+  "AWEMMY.Roll.KnowledgeBonus": "Item Bonus",
   "AWEMMY.Roll.Formula": "Formula",
   "AWEMMY.Roll.DC": "DC",
   "AWEMMY.Roll.Visibility": "Visibility",
@@ -79,7 +86,8 @@
   "AWEMMY.Character.HPTemp": "Temp HP",
   "AWEMMY.Character.FlowPoints": "Flow Points",
   "AWEMMY.Character.FlowPointsTemp": "Temp FP",
-  "AWEMMY.Character.BoostLevel": "Boost Level",
+  "AWEMMY.Character.BoostLevel": "Boost",
+  "AWEMMY.Character.Repertoire": "Repertoire",
   "AWEMMY.Character.Mod": "MOD",
   "AWEMMY.Character.DC": "DC",
   "AWEMMY.Character.Bonus": "+/−",
diff --git a/module/applications/sheets/character-sheet.mjs b/module/applications/sheets/character-sheet.mjs
index be2a5b8..03ceb20 100644
--- a/module/applications/sheets/character-sheet.mjs
+++ b/module/applications/sheets/character-sheet.mjs
@@ -100,6 +100,11 @@ export default class AwECharacterSheet extends AwEActorSheet {
           img: `systems/fvtt-adventures-with-emmy/assets/conditions/${c.id}.svg`,
           active: doc.statuses.has(c.id)
         }))
+        context.inhibitedActive = doc.statuses.has("inhibited")
+        context.vulnerableActive = doc.statuses.has("vulnerable")
+        context.inhibitedPenalty = doc.system.inhibitedPenalty
+        context.vulnerablePenalty = doc.system.vulnerablePenalty
+        context.hasConditionPenalties = context.inhibitedActive || context.vulnerableActive
         break
       case "biography":
         context.tab = context.tabs.biography
diff --git a/module/documents/actor.mjs b/module/documents/actor.mjs
index 8b1064a..03c5049 100644
--- a/module/documents/actor.mjs
+++ b/module/documents/actor.mjs
@@ -44,11 +44,7 @@ export default class AwEActor extends Actor {
     const attribute = this.system.attributes[attrId]
     if (!attribute) return null
 
-    const knowledgeBonuses = this.itemTypes.field?.map(f => ({
-      label: f.name,
-      bonus: f.system.knowledgeBonus ?? ""
-    })).filter(f => f.bonus !== "") ?? []
-
+    const knowledgeBonuses = this.#buildItemBonuses()
     const { conditionBonus, conditionLabels } = this.#buildConditionOptions()
 
     const roll = await AwERoll.prompt({
@@ -101,12 +97,7 @@ export default class AwEActor extends Actor {
     const attribute = this.system.attributes[attributeId]
     if (!attribute) return null
 
-    // Collect knowledge bonuses from embedded Field items
-    const knowledgeBonuses = this.itemTypes.field?.map(f => ({
-      label: f.name,
-      bonus: f.system.knowledgeBonus ?? ""
-    })).filter(f => f.bonus !== "") ?? []
-
+    const knowledgeBonuses = this.#buildItemBonuses()
     const { conditionBonus, conditionLabels } = this.#buildConditionOptions()
 
     const roll = await AwERoll.prompt({
@@ -127,6 +118,19 @@ export default class AwEActor extends Actor {
     return roll
   }
 
+  /** Collect roll bonuses from all item types that declare a rollBonus or knowledgeBonus. */
+  #buildItemBonuses() {
+    const entries = [
+      // Field items use the original knowledgeBonus field
+      ...(this.itemTypes.field ?? []).map(i => ({ label: i.name, bonus: i.system.knowledgeBonus ?? "" })),
+      // Ability, equipment, specialization use rollBonus
+      ...(this.itemTypes.ability ?? []).map(i => ({ label: i.name, bonus: i.system.rollBonus ?? "" })),
+      ...(this.itemTypes.equipment ?? []).map(i => ({ label: i.name, bonus: i.system.rollBonus ?? "" })),
+      ...(this.itemTypes.specialization ?? []).map(i => ({ label: i.name, bonus: i.system.rollBonus ?? "" })),
+    ]
+    return entries.filter(e => e.bonus !== "")
+  }
+
   #buildConditionOptions() {
     let conditionBonus = 0
     const conditionLabels = []
@@ -142,6 +146,11 @@ export default class AwEActor extends Actor {
       conditionBonus -= 2
       conditionLabels.push({ label: game.i18n.localize("AWEMMY.Condition.Jumbled"), bonus: -2 })
     }
+    if (this.statuses.has("inhibited")) {
+      const penalty = this.system.inhibitedPenalty ?? 2
+      conditionBonus -= penalty
+      conditionLabels.push({ label: game.i18n.localize("AWEMMY.Condition.Inhibited"), bonus: -penalty })
+    }
     return { conditionBonus, conditionLabels }
   }
 
diff --git a/module/documents/roll.mjs b/module/documents/roll.mjs
index 6cb1bc6..a4a5cf6 100644
--- a/module/documents/roll.mjs
+++ b/module/documents/roll.mjs
@@ -25,6 +25,7 @@ export default class AwERoll extends Roll {
   get damageCritical()    { return this.options.damageCritical ?? false }
   get conditionBonus()    { return this.options.conditionBonus ?? 0 }
   get conditionLabels()   { return this.options.conditionLabels ?? [] }
+  get rollTwice()         { return this.options.rollTwice ?? "" }
 
   // --- Outcome calculation ---
 
@@ -116,17 +117,23 @@ export default class AwERoll extends Roll {
         const el            = dialog.element
         const bonusSelect   = el.querySelector('#awe-bonus')
         const knowledgeSel  = el.querySelector('#awe-knowledge')
+        const rollTwiceSel  = el.querySelector('#awe-roll-twice')
         const preview       = el.querySelector('#awe-formula-preview')
+        const diceExprEl    = el.querySelector('#awe-dice-expr')
         function updatePreview() {
           const sit   = parseInt(bonusSelect?.value) || 0
           const kn    = parseInt(knowledgeSel?.value) || 0
           const total = baseMod + sit + kn
           const sign  = total >= 0 ? '+' : '−'
           const abs   = Math.abs(total)
-          preview.textContent = total === 0 ? '1d20' : `1d20 ${sign} ${abs}`
+          const mode  = rollTwiceSel?.value
+          const dice  = mode === 'higher' ? '2d20kh1' : mode === 'lower' ? '2d20kl1' : '1d20'
+          if (diceExprEl) diceExprEl.textContent = dice
+          preview.textContent = total === 0 ? dice : `${dice} ${sign} ${abs}`
         }
         bonusSelect?.addEventListener('change', updatePreview)
         knowledgeSel?.addEventListener('change', updatePreview)
+        rollTwiceSel?.addEventListener('change', updatePreview)
         updatePreview()
       },
       buttons: [{
@@ -146,10 +153,16 @@ export default class AwERoll extends Roll {
     const knowledgeBonus = parseInt(result.knowledgeBonus) || 0
     const dc             = result.dc !== "" ? parseInt(result.dc) : undefined
     const rollMode       = result.visibility ?? game.settings.get("core", "rollMode")
+    const rollTwice      = result.rollTwice ?? ""
 
-    // Formula: 1d20 + (mod + attrBonus) [± bonus] [± knowledgeBonus] [± conditionBonus]
+    // Dice expression based on roll-twice mode
+    const diceExpr = rollTwice === 'higher' ? '2d20kh1'
+                   : rollTwice === 'lower'  ? '2d20kl1'
+                   : '1d20'
+
+    // Formula: {diceExpr} + (mod + attrBonus) [± bonus] [± knowledgeBonus] [± conditionBonus]
     const totalMod = mod + attrBonus + bonus + knowledgeBonus + (options.conditionBonus ?? 0)
-    let formula = `1d20`
+    let formula = diceExpr
     if (totalMod > 0)      formula += ` + ${totalMod}`
     else if (totalMod < 0) formula += ` - ${Math.abs(totalMod)}`
 
@@ -162,6 +175,7 @@ export default class AwERoll extends Roll {
       knowledgeBonus,
       conditionBonus:  options.conditionBonus ?? 0,
       conditionLabels: options.conditionLabels ?? [],
+      rollTwice,
       dc,
       actorId:          options.actorId,
       actorName:        options.actorName,
@@ -175,8 +189,9 @@ export default class AwERoll extends Roll {
     await roll.evaluate()
 
     // Compute degree of success when a DC is known
+    // Use the *kept* die result (active:true) for nat-20/nat-1 adjustment
     if (dc !== undefined) {
-      const d20Value = roll.dice[0]?.results[0]?.result ?? 0
+      const d20Value = roll.dice[0]?.results.find(r => r.active)?.result ?? 0
       roll.options.outcome = AwERoll.computeOutcome(roll.total, dc, d20Value)
     }
 
@@ -220,6 +235,7 @@ export default class AwERoll extends Roll {
         conditionBonus:   isPrivate ? null : this.conditionBonus,
         conditionLabels:  this.conditionLabels,
         dice:          this.dice,
+        rollTwice:     this.rollTwice,
         outcome:       isPrivate ? null : this.outcome,
         dc:            this.dc,
         actorId:        this.actorId,
diff --git a/module/models/ability.mjs b/module/models/ability.mjs
index 2779b0c..fdcea2f 100644
--- a/module/models/ability.mjs
+++ b/module/models/ability.mjs
@@ -28,6 +28,7 @@ export default class AwEAbility extends foundry.abstract.TypeDataModel {
     schema.isDaily = new fields.BooleanField({ required: true, initial: false })
     schema.flowPointCost = new fields.NumberField({ required: true, nullable: false, initial: 0, min: 0, integer: true })
     schema.usedToday = new fields.BooleanField({ required: true, initial: false })
+    schema.rollBonus = new fields.StringField({ initial: "", required: false, nullable: true })
 
     return schema
   }
diff --git a/module/models/character.mjs b/module/models/character.mjs
index 4a881fc..1e7aad6 100644
--- a/module/models/character.mjs
+++ b/module/models/character.mjs
@@ -51,6 +51,10 @@ export default class AwECharacter extends foundry.abstract.TypeDataModel {
       }, {})
     )
 
+    // Condition penalty magnitudes (used when the respective condition is active)
+    schema.inhibitedPenalty = new fields.NumberField({ required: true, nullable: false, integer: true, initial: 2, min: 0 })
+    schema.vulnerablePenalty = new fields.NumberField({ required: true, nullable: false, integer: true, initial: 2, min: 0 })
+
     return schema
   }
 
diff --git a/module/models/equipment.mjs b/module/models/equipment.mjs
index 0522c7d..0f5218f 100644
--- a/module/models/equipment.mjs
+++ b/module/models/equipment.mjs
@@ -7,6 +7,7 @@ export default class AwEEquipment extends foundry.abstract.TypeDataModel {
     schema.description = new fields.HTMLField({ required: true, textSearch: true })
     schema.quantity = new fields.NumberField({ ...requiredInteger, initial: 1, min: 0 })
     schema.weight = new fields.NumberField({ required: true, nullable: false, initial: 0, min: 0 })
+    schema.rollBonus = new fields.StringField({ initial: "", required: false, nullable: true })
 
     return schema
   }
diff --git a/module/models/specialization.mjs b/module/models/specialization.mjs
index 53ad326..3bc44b6 100644
--- a/module/models/specialization.mjs
+++ b/module/models/specialization.mjs
@@ -25,6 +25,7 @@ export default class AwESpecialization extends foundry.abstract.TypeDataModel {
 
     schema.description = new fields.HTMLField({ required: true, textSearch: true })
     schema.traits = new fields.ArrayField(new fields.StringField())
+    schema.rollBonus = new fields.StringField({ initial: "", required: false, nullable: true })
 
     return schema
   }
diff --git a/templates/ability.hbs b/templates/ability.hbs
index 25f420e..e3f3749 100644
--- a/templates/ability.hbs
+++ b/templates/ability.hbs
@@ -57,6 +57,11 @@
       </div>
     </div>
 
+    <div class="form-group">
+      <label>{{localize "AWEMMY.Item.RollBonus"}}</label>
+      {{formInput systemFields.rollBonus value=system.rollBonus placeholder="e.g. 2 to Recall Knowledge"}}
+    </div>
+
     <div class="form-group-tags">
       <label>{{localize "AWEMMY.Ability.Traits"}}</label>
       <div class="tags-list">
diff --git a/templates/character-biography.hbs b/templates/character-biography.hbs
index c1b99be..26ba96a 100644
--- a/templates/character-biography.hbs
+++ b/templates/character-biography.hbs
@@ -6,10 +6,22 @@
       <label>{{localize "AWEMMY.Character.Pronouns"}}</label>
       {{formInput systemFields.pronouns value=system.pronouns disabled=isPlayMode}}
     </div>
-    <div class="form-group">
-      <label>{{localize "AWEMMY.Character.Specialization"}}</label>
-      {{formInput systemFields.specialization value=system.specialization disabled=isPlayMode}}
+  </fieldset>
+
+  <!-- Background (max 1) -->
+  <fieldset class="items-list-fieldset">
+    <legend>{{localize "AWEMMY.Item.Background"}}</legend>
+    {{#each backgrounds}}
+    <div class="item-row" data-item-id="{{id}}" data-item-uuid="{{uuid}}" data-drag="true" data-tooltip="{{itemTooltip this}}">
+      <img src="{{img}}" class="item-img" alt="{{name}}" />
+      <span class="item-name">{{name}}</span>
+      <div class="item-controls">
+        <a class="item-control" data-action="edit" data-item-id="{{id}}" data-item-uuid="{{uuid}}" data-tooltip="{{localize 'AWEMMY.Sheet.EditItem'}}"><i class="fas fa-edit"></i></a>
+        <a class="item-control" data-action="delete" data-item-id="{{id}}" data-item-uuid="{{uuid}}" data-tooltip="{{localize 'AWEMMY.Sheet.DeleteItem'}}"><i class="fas fa-trash"></i></a>
+      </div>
     </div>
+    {{/each}}
+    {{#unless backgrounds.length}}<div class="item-row item-empty"><em>{{localize "AWEMMY.Character.DropBackground"}}</em></div>{{/unless}}
   </fieldset>
 
   <!-- Field (max 1) -->
@@ -81,22 +93,6 @@
     {{#unless archetypes.length}}<div class="item-row item-empty"><em>{{localize "AWEMMY.Character.DropArchetype"}}</em></div>{{/unless}}
   </fieldset>
 
-  <!-- Background (max 1) -->
-  <fieldset class="items-list-fieldset">
-    <legend>{{localize "AWEMMY.Item.Background"}}</legend>
-    {{#each backgrounds}}
-    <div class="item-row" data-item-id="{{id}}" data-item-uuid="{{uuid}}" data-drag="true" data-tooltip="{{itemTooltip this}}">
-      <img src="{{img}}" class="item-img" alt="{{name}}" />
-      <span class="item-name">{{name}}</span>
-      <div class="item-controls">
-        <a class="item-control" data-action="edit" data-item-id="{{id}}" data-item-uuid="{{uuid}}" data-tooltip="{{localize 'AWEMMY.Sheet.EditItem'}}"><i class="fas fa-edit"></i></a>
-        <a class="item-control" data-action="delete" data-item-id="{{id}}" data-item-uuid="{{uuid}}" data-tooltip="{{localize 'AWEMMY.Sheet.DeleteItem'}}"><i class="fas fa-trash"></i></a>
-      </div>
-    </div>
-    {{/each}}
-    {{#unless backgrounds.length}}<div class="item-row item-empty"><em>{{localize "AWEMMY.Character.DropBackground"}}</em></div>{{/unless}}
-  </fieldset>
-
   <fieldset>
     <legend>{{localize "AWEMMY.Character.Description"}}</legend>
     {{formInput
diff --git a/templates/character-main.hbs b/templates/character-main.hbs
index 93ec95d..642f5c8 100644
--- a/templates/character-main.hbs
+++ b/templates/character-main.hbs
@@ -48,7 +48,7 @@
 
   {{!-- Abilities --}}
   <fieldset>
-    <legend>{{localize "AWEMMY.Item.Ability"}}</legend>
+    <legend>{{localize "AWEMMY.Character.Repertoire"}}</legend>
     <div class="item-list">
       {{#each abilities as |item|}}
       <div class="item-row {{#if item.usedToday}}ability-used{{/if}}" data-drag="true" data-item-id="{{item.id}}" data-item-uuid="{{item.uuid}}" data-tooltip="{{itemTooltip item}}">
@@ -95,6 +95,22 @@
       </a>
       {{/each}}
     </div>
+    {{#if hasConditionPenalties}}
+    <div class="condition-penalties">
+      {{#if inhibitedActive}}
+      <div class="condition-penalty-row">
+        <label>{{localize "AWEMMY.Condition.Inhibited"}} {{localize "AWEMMY.Condition.Penalty"}}</label>
+        {{formInput systemFields.inhibitedPenalty value=inhibitedPenalty classes="condition-penalty-input"}}
+      </div>
+      {{/if}}
+      {{#if vulnerableActive}}
+      <div class="condition-penalty-row">
+        <label>{{localize "AWEMMY.Condition.Vulnerable"}} {{localize "AWEMMY.Condition.DCPenalty"}}</label>
+        {{formInput systemFields.vulnerablePenalty value=vulnerablePenalty classes="condition-penalty-input"}}
+      </div>
+      {{/if}}
+    </div>
+    {{/if}}
   </fieldset>
 
 </section>
diff --git a/templates/chat-message.hbs b/templates/chat-message.hbs
index b1009ec..755a8c0 100644
--- a/templates/chat-message.hbs
+++ b/templates/chat-message.hbs
@@ -25,7 +25,7 @@
   <div class="roll-breakdown">
     {{#each dice}}
     {{#each results}}
-    <span class="die-result {{#if (eq result ../faces)}}max{{else if (eq result 1)}}min{{/if}}">
+    <span class="die-result {{#unless active}}discarded{{else}}{{#if (eq result ../faces)}}max{{else if (eq result 1)}}min{{/if}}{{/unless}}">
       <i class="fa-solid fa-dice-d{{../faces}}"></i> {{result}}
     </span>
     {{/each}}
@@ -55,6 +55,15 @@
     {{#if dc}}<span class="roll-dc">/ DC {{dc}}</span>{{/if}}
   </div>
 
+  {{!-- Roll-twice mode badge --}}
+  {{#if rollTwice}}
+  <div class="roll-twice-badge">
+    {{#if (eq rollTwice "higher")}}<i class="fas fa-angles-up"></i> {{localize "AWEMMY.Roll.TakeHigher"}}
+    {{else}}<i class="fas fa-angles-down"></i> {{localize "AWEMMY.Roll.TakeLower"}}
+    {{/if}}
+  </div>
+  {{/if}}
+
   {{!-- Outcome badge --}}
   {{#if outcome}}
   <div class="outcome-badge {{outcome}}">
diff --git a/templates/equipment.hbs b/templates/equipment.hbs
index 41cac37..8b0472a 100644
--- a/templates/equipment.hbs
+++ b/templates/equipment.hbs
@@ -16,6 +16,11 @@
       </div>
     </div>
 
+    <div class="form-group">
+      <label>{{localize "AWEMMY.Item.RollBonus"}}</label>
+      {{formInput systemFields.rollBonus value=system.rollBonus placeholder="e.g. 2 to Recall Knowledge"}}
+    </div>
+
     <fieldset>
       <legend>{{localize "AWEMMY.Item.Description"}}</legend>
       {{formInput systemFields.description enriched=enrichedDescription value=system.description name="system.description" toggled=true}}
diff --git a/templates/roll-dialog.hbs b/templates/roll-dialog.hbs
index c156059..e94b9c2 100644
--- a/templates/roll-dialog.hbs
+++ b/templates/roll-dialog.hbs
@@ -4,7 +4,7 @@
   <div class="roll-header">
     <span class="roll-attr-name">{{attrLabel}}</span>
     <span class="roll-formula-summary">
-      1d20
+      <span id="awe-dice-expr">1d20</span>
       {{#if (gt modifier 0)}} + {{modifier}}{{else if (lt modifier 0)}} − {{abs modifier}}{{/if}}
       {{#if (gt attributeBonus 0)}} + <em>{{attributeBonus}}</em>{{else if (lt attributeBonus 0)}} − <em>{{abs attributeBonus}}</em>{{/if}}
     </span>
@@ -20,6 +20,16 @@
   </div>
   {{/if}}
 
+  {{!-- Roll twice --}}
+  <div class="dialog-row">
+    <label for="awe-roll-twice">{{localize "AWEMMY.Roll.RollTwice"}}</label>
+    <select id="awe-roll-twice" name="rollTwice">
+      <option value="">{{localize "AWEMMY.Roll.Normal"}}</option>
+      <option value="higher">{{localize "AWEMMY.Roll.TakeHigher"}}</option>
+      <option value="lower">{{localize "AWEMMY.Roll.TakeLower"}}</option>
+    </select>
+  </div>
+
   {{!-- Situational bonus / penalty --}}
   <div class="dialog-row">
     <label for="awe-bonus">{{localize "AWEMMY.Roll.SituationalBonus"}}</label>
diff --git a/templates/specialization.hbs b/templates/specialization.hbs
index d14cef0..e0a3eff 100644
--- a/templates/specialization.hbs
+++ b/templates/specialization.hbs
@@ -31,6 +31,11 @@
       </div>
     </div>
 
+    <div class="form-group">
+      <label>{{localize "AWEMMY.Item.RollBonus"}}</label>
+      {{formInput systemFields.rollBonus value=system.rollBonus placeholder="e.g. 2 to Recall Knowledge"}}
+    </div>
+
     <fieldset>
       <legend>{{localize "AWEMMY.Item.Description"}}</legend>
       {{formInput systemFields.description enriched=enrichedDescription value=system.description name="system.description" toggled=true}}