diff --git a/src/actions/Clear.ts b/src/actions/Clear.ts
index c51d64d404..bb57eeed7e 100644
--- a/src/actions/Clear.ts
+++ b/src/actions/Clear.ts
@@ -1,4 +1,4 @@
-import PlainTarget from "../processTargets/targets/PlainTarget";
+import { PlainTarget } from "../processTargets/targets";
 import { Target } from "../typings/target.types";
 import { Graph } from "../typings/Types";
 import { setSelectionsAndFocusEditor } from "../util/setSelectionsAndFocusEditor";
diff --git a/src/actions/CutCopy.ts b/src/actions/CutCopy.ts
index fa540683c6..a60051647f 100644
--- a/src/actions/CutCopy.ts
+++ b/src/actions/CutCopy.ts
@@ -1,4 +1,4 @@
-import PlainTarget from "../processTargets/targets/PlainTarget";
+import { PlainTarget } from "../processTargets/targets";
 import { Target } from "../typings/target.types";
 import { Graph } from "../typings/Types";
 import { getOutsideOverflow } from "../util/targetUtils";
diff --git a/src/actions/EditNew/runNotebookCellTargets.ts b/src/actions/EditNew/runNotebookCellTargets.ts
index dfd58107bd..f8ac4bdc7a 100644
--- a/src/actions/EditNew/runNotebookCellTargets.ts
+++ b/src/actions/EditNew/runNotebookCellTargets.ts
@@ -1,5 +1,5 @@
 import { commands, Selection } from "vscode";
-import { NotebookCellPositionTarget } from "../../processTargets/targets/NotebookCellTarget";
+import { NotebookCellPositionTarget } from "../../processTargets/targets";
 import { Target } from "../../typings/target.types";
 import { Graph } from "../../typings/Types";
 import { createThatMark, ensureSingleTarget } from "../../util/targetUtils";
diff --git a/src/processTargets/marks/CursorStage.ts b/src/processTargets/marks/CursorStage.ts
index 71a4727fb8..3c2e8e9363 100644
--- a/src/processTargets/marks/CursorStage.ts
+++ b/src/processTargets/marks/CursorStage.ts
@@ -4,17 +4,21 @@ import { ProcessedTargetsContext } from "../../typings/Types";
 import { isReversed } from "../../util/selectionUtils";
 import { MarkStage } from "../PipelineStages.types";
 import WeakTarget from "../targets/WeakTarget";
+import TokenTarget from "../targets/TokenTarget";
 
 export default class CursorStage implements MarkStage {
   constructor(_modifier: CursorMark) {}
 
   run(context: ProcessedTargetsContext): Target[] {
     return context.currentSelections.map((selection) => {
-      return new WeakTarget({
+      const parameters = {
         editor: selection.editor,
         isReversed: isReversed(selection.selection),
         contentRange: selection.selection,
-      });
+      };
+      return selection.selection.isEmpty
+        ? new WeakTarget(parameters)
+        : new TokenTarget(parameters);
     });
   }
 }
diff --git a/src/processTargets/marks/DecoratedSymbolStage.ts b/src/processTargets/marks/DecoratedSymbolStage.ts
index 76050d95a3..59b25dacd6 100644
--- a/src/processTargets/marks/DecoratedSymbolStage.ts
+++ b/src/processTargets/marks/DecoratedSymbolStage.ts
@@ -2,7 +2,7 @@ import { Target } from "../../typings/target.types";
 import { DecoratedSymbolMark } from "../../typings/targetDescriptor.types";
 import { ProcessedTargetsContext } from "../../typings/Types";
 import { MarkStage } from "../PipelineStages.types";
-import WeakTarget from "../targets/WeakTarget";
+import { WeakTarget } from "../targets";
 
 export default class implements MarkStage {
   constructor(private modifier: DecoratedSymbolMark) {}
diff --git a/src/processTargets/modifiers/ItemStage/ItemStage.ts b/src/processTargets/modifiers/ItemStage/ItemStage.ts
index 6d0d83feaf..b7d2b7e77a 100644
--- a/src/processTargets/modifiers/ItemStage/ItemStage.ts
+++ b/src/processTargets/modifiers/ItemStage/ItemStage.ts
@@ -10,7 +10,7 @@ import { ProcessedTargetsContext } from "../../../typings/Types";
 import { getInsertionDelimiter } from "../../../util/nodeSelectors";
 import { getRangeLength } from "../../../util/rangeUtils";
 import { ModifierStage } from "../../PipelineStages.types";
-import ScopeTypeTarget from "../../targets/ScopeTypeTarget";
+import { ScopeTypeTarget } from "../../targets";
 import ContainingSyntaxScopeStage, {
   SimpleContainingScopeModifier,
 } from "../scopeTypeStages/ContainingSyntaxScopeStage";
diff --git a/src/processTargets/modifiers/LeadingTrailingStages.ts b/src/processTargets/modifiers/LeadingTrailingStages.ts
index 0494e08290..961b1088ff 100644
--- a/src/processTargets/modifiers/LeadingTrailingStages.ts
+++ b/src/processTargets/modifiers/LeadingTrailingStages.ts
@@ -5,16 +5,19 @@ import {
 } from "../../typings/targetDescriptor.types";
 import { ProcessedTargetsContext } from "../../typings/Types";
 import { ModifierStage } from "../PipelineStages.types";
+import { weakContainingTokenStage } from "./commonWeakContainingScopeStages";
 
 export class LeadingStage implements ModifierStage {
   constructor(private modifier: LeadingModifier) {}
 
   run(context: ProcessedTargetsContext, target: Target): Target[] {
-    const leading = target.getLeadingDelimiterTarget();
-    if (leading == null) {
-      throw Error("No available leading range");
-    }
-    return [leading];
+    return weakContainingTokenStage.run(context, target).map((target) => {
+      const leading = target.getLeadingDelimiterTarget();
+      if (leading == null) {
+        throw Error("No available leading delimiter range");
+      }
+      return leading;
+    });
   }
 }
 
@@ -22,10 +25,12 @@ export class TrailingStage implements ModifierStage {
   constructor(private modifier: TrailingModifier) {}
 
   run(context: ProcessedTargetsContext, target: Target): Target[] {
-    const trailing = target.getTrailingDelimiterTarget();
-    if (trailing == null) {
-      throw Error("No available trailing range");
-    }
-    return [trailing];
+    return weakContainingTokenStage.run(context, target).map((target) => {
+      const trailing = target.getTrailingDelimiterTarget();
+      if (trailing == null) {
+        throw Error("No available trailing delimiter range");
+      }
+      return trailing;
+    });
   }
 }
diff --git a/src/processTargets/modifiers/commonWeakContainingScopeStages.ts b/src/processTargets/modifiers/commonWeakContainingScopeStages.ts
index 7f6d45e6f9..487d76dd08 100644
--- a/src/processTargets/modifiers/commonWeakContainingScopeStages.ts
+++ b/src/processTargets/modifiers/commonWeakContainingScopeStages.ts
@@ -15,3 +15,11 @@ export const weakContainingLineStage = new ModifyIfWeakStage({
     scopeType: { type: "line" },
   },
 });
+
+export const weakContainingTokenStage = new ModifyIfWeakStage({
+  type: "modifyIfWeak",
+  modifier: {
+    type: "containingScope",
+    scopeType: { type: "token" },
+  },
+});
diff --git a/src/processTargets/modifiers/scopeTypeStages/TokenStage.ts b/src/processTargets/modifiers/scopeTypeStages/TokenStage.ts
index bcd15861f2..233064a2d8 100644
--- a/src/processTargets/modifiers/scopeTypeStages/TokenStage.ts
+++ b/src/processTargets/modifiers/scopeTypeStages/TokenStage.ts
@@ -7,7 +7,7 @@ import {
 import { ProcessedTargetsContext } from "../../../typings/Types";
 import { getTokensInRange, PartialToken } from "../../../util/getTokensInRange";
 import { ModifierStage } from "../../PipelineStages.types";
-import TokenTarget from "../../targets/TokenTarget";
+import { TokenTarget } from "../../targets";
 
 export default class implements ModifierStage {
   constructor(private modifier: ContainingScopeModifier | EveryScopeModifier) {}
diff --git a/src/processTargets/processTargets.ts b/src/processTargets/processTargets.ts
index ec51362e61..bb56993ed7 100644
--- a/src/processTargets/processTargets.ts
+++ b/src/processTargets/processTargets.ts
@@ -12,8 +12,7 @@ import { ensureSingleEditor } from "../util/targetUtils";
 import getMarkStage from "./getMarkStage";
 import getModifierStage from "./getModifierStage";
 import { ModifierStage } from "./PipelineStages.types";
-import PlainTarget from "./targets/PlainTarget";
-import PositionTarget from "./targets/PositionTarget";
+import { PlainTarget, PositionTarget } from "./targets";
 
 /**
  * Converts the abstract target descriptions provided by the user to a concrete
diff --git a/src/processTargets/targets/TokenTarget.ts b/src/processTargets/targets/TokenTarget.ts
index c19c77f175..fab6e3992f 100644
--- a/src/processTargets/targets/TokenTarget.ts
+++ b/src/processTargets/targets/TokenTarget.ts
@@ -1,11 +1,11 @@
 import { Range } from "vscode";
+import { BaseTarget } from ".";
 import { Target } from "../../typings/target.types";
 import {
   getTokenLeadingDelimiterTarget,
   getTokenRemovalRange,
   getTokenTrailingDelimiterTarget,
 } from "../targetUtil/insertionRemovalBehaviors/TokenInsertionRemovalBehavior";
-import BaseTarget from "./BaseTarget";
 
 export default class TokenTarget extends BaseTarget {
   insertionDelimiter = " ";
diff --git a/src/test/suite/fixtures/recorded/selectionTypes/clearLeading.yml b/src/test/suite/fixtures/recorded/selectionTypes/clearLeading.yml
new file mode 100644
index 0000000000..c985780699
--- /dev/null
+++ b/src/test/suite/fixtures/recorded/selectionTypes/clearLeading.yml
@@ -0,0 +1,25 @@
+languageId: plaintext
+command:
+  spokenForm: clear leading
+  version: 2
+  targets:
+    - type: primitive
+      modifiers:
+        - {type: leading}
+  usePrePhraseSnapshot: true
+  action: {name: clearAndSetSelection}
+initialState:
+  documentContents: aaa bbb ccc
+  selections:
+    - anchor: {line: 0, character: 6}
+      active: {line: 0, character: 6}
+  marks: {}
+finalState:
+  documentContents: aaabbb ccc
+  selections:
+    - anchor: {line: 0, character: 3}
+      active: {line: 0, character: 3}
+  thatMark:
+    - anchor: {line: 0, character: 3}
+      active: {line: 0, character: 3}
+fullTargets: [{type: primitive, mark: {type: cursor}, modifiers: [{type: leading}]}]
diff --git a/src/test/suite/fixtures/recorded/selectionTypes/clearTrailing.yml b/src/test/suite/fixtures/recorded/selectionTypes/clearTrailing.yml
new file mode 100644
index 0000000000..3a40f79e01
--- /dev/null
+++ b/src/test/suite/fixtures/recorded/selectionTypes/clearTrailing.yml
@@ -0,0 +1,25 @@
+languageId: plaintext
+command:
+  spokenForm: clear trailing
+  version: 2
+  targets:
+    - type: primitive
+      modifiers:
+        - {type: trailing}
+  usePrePhraseSnapshot: true
+  action: {name: clearAndSetSelection}
+initialState:
+  documentContents: aaa bbb ccc
+  selections:
+    - anchor: {line: 0, character: 6}
+      active: {line: 0, character: 6}
+  marks: {}
+finalState:
+  documentContents: aaa bbbccc
+  selections:
+    - anchor: {line: 0, character: 7}
+      active: {line: 0, character: 7}
+  thatMark:
+    - anchor: {line: 0, character: 7}
+      active: {line: 0, character: 7}
+fullTargets: [{type: primitive, mark: {type: cursor}, modifiers: [{type: trailing}]}]
diff --git a/src/util/tryConstructTarget.ts b/src/util/tryConstructTarget.ts
index 220489f7c2..3a2bb0af29 100644
--- a/src/util/tryConstructTarget.ts
+++ b/src/util/tryConstructTarget.ts
@@ -1,7 +1,9 @@
 import { Range, TextEditor } from "vscode";
-import { CommonTargetParameters } from "../processTargets/targets/BaseTarget";
-import LineTarget from "../processTargets/targets/LineTarget";
-import PlainTarget from "../processTargets/targets/PlainTarget";
+import {
+  CommonTargetParameters,
+  LineTarget,
+  PlainTarget,
+} from "../processTargets/targets";
 import { Target } from "../typings/target.types";
 
 type TargetConstructor<T extends Target> = new (