diff --git a/web/app/components/inputs/people-select.hbs b/web/app/components/inputs/people-select.hbs
index e47736539..7a685266f 100644
--- a/web/app/components/inputs/people-select.hbs
+++ b/web/app/components/inputs/people-select.hbs
@@ -14,17 +14,21 @@
   @onKeydown={{@onKeydown}}
   @disabled={{@disabled}}
   @selectedItemComponent={{component "multiselect/user-email-image-chip"}}
+  @calculatePosition={{this.calculatePosition}}
+  @loadingMessage="Loading..."
+  @eventType="click"
+  {{on "click" this.onClick}}
   ...attributes
   as |value|
 >
   <div class="flex items-center gap-2 overflow-hidden py-1">
-    <Person::Avatar @email={{value}} @size="medium" class="shrink-0" />
-    <div class="w-full">
-      <div class="text-body-100 leading-tight">
+    <Person::Avatar @email={{value}} />
+    <div class="w-full min-w-0">
+      <div class="truncate text-body-200 leading-tight">
         {{get-model-attr "person.name" value}}
-      </div>
-      <div class="text-body-100 leading-tight opacity-70">
-        {{get-model-attr "person.email" value}}
+        <span class="ml-0.5 text-body-100 text-color-foreground-disabled">
+          {{get-model-attr "person.email" value}}
+        </span>
       </div>
     </div>
   </div>
diff --git a/web/app/components/inputs/people-select.ts b/web/app/components/inputs/people-select.ts
index d2283708a..67ae69c4a 100644
--- a/web/app/components/inputs/people-select.ts
+++ b/web/app/components/inputs/people-select.ts
@@ -8,6 +8,10 @@ import FetchService from "hermes/services/fetch";
 import Ember from "ember";
 import StoreService from "hermes/services/store";
 import PersonModel from "hermes/models/person";
+import { Select } from "ember-power-select/components/power-select";
+import { next } from "@ember/runloop";
+import calculatePosition from "ember-basic-dropdown/utils/calculate-position";
+import { assert } from "@ember/debug";
 
 export interface GoogleUser {
   emailAddresses: { value: string }[];
@@ -15,6 +19,26 @@ export interface GoogleUser {
   photos: { url: string }[];
 }
 
+enum ComputedVerticalPosition {
+  Above = "above",
+  Below = "below",
+}
+
+enum ComputedHorizontalPosition {
+  Left = "left",
+  Right = "right",
+}
+
+interface CalculatePositionOptions {
+  horizontalPosition: ComputedHorizontalPosition;
+  verticalPosition: ComputedVerticalPosition;
+  matchTriggerWidth: boolean;
+  previousHorizontalPosition?: ComputedHorizontalPosition;
+  previousVerticalPosition?: ComputedVerticalPosition;
+  renderInPlace: boolean;
+  dropdown: any;
+}
+
 interface InputsPeopleSelectComponentSignature {
   Element: HTMLDivElement;
   Args: {
@@ -40,15 +64,39 @@ export default class InputsPeopleSelectComponent extends Component<InputsPeopleS
    */
   @tracked protected people: string[] = [];
 
+  /**
+   * The action to run when the PowerSelect input is clicked.
+   * Prevents the dropdown from opening when the input is empty.
+   */
+  @action protected onClick(e: MouseEvent) {
+    const target = e.target as HTMLElement;
+    const input = target.closest(".ember-power-select-trigger") as HTMLElement;
+
+    if (input) {
+      const value = input.querySelector("input")?.value;
+      if (value === "") {
+        e.stopImmediatePropagation();
+      }
+    }
+  }
+
   /**
    * An action occurring on every keystroke.
    * Handles cases where the user clears the input,
    * since `onChange` is not called in that case.
    * See: https://ember-power-select.com/docs/custom-search-action
    */
-  @action onInput(inputValue: string) {
+  @action protected onInput(inputValue: string, select: Select) {
     if (inputValue === "") {
       this.people = [];
+
+      /**
+       * Stop the redundant "type to search" message
+       * from appearing when the last character is deleted.
+       */
+      next(() => {
+        select.actions.close();
+      });
     }
   }
 
@@ -56,10 +104,58 @@ export default class InputsPeopleSelectComponent extends Component<InputsPeopleS
    * The action taken when focus leaves the component.
    * Clears the people list and calls `this.args.onBlur` if it exists.
    */
-  @action onClose() {
+  @action protected onClose() {
     this.people = [];
   }
 
+  /**
+   * Custom position-calculating function for the dropdown.
+   * Ensures the dropdown is at least 320px wide, instead of 100% of the trigger.
+   * Improves dropdown appearance when the trigger is small, e.g., in the sidebar.
+   */
+  @action protected calculatePosition(
+    trigger: HTMLElement,
+    content: HTMLElement,
+    destination: HTMLElement,
+    options: CalculatePositionOptions,
+  ) {
+    const position = calculatePosition(trigger, content, destination, options);
+
+    const extraOffsetLeft = 4;
+    const extraOffsetBelow = 2;
+    const extraOffsetAbove = extraOffsetBelow + 2;
+
+    const { verticalPosition, horizontalPosition } = position;
+
+    let { top, left, width } = position.style;
+
+    assert("top must be a number", typeof top === "number");
+    assert("left must be a number", typeof left === "number");
+    assert("width must be a number", typeof width === "number");
+
+    switch (verticalPosition) {
+      case ComputedVerticalPosition.Above:
+        top -= extraOffsetAbove;
+        break;
+      case ComputedVerticalPosition.Below:
+        top += extraOffsetBelow;
+        break;
+    }
+
+    switch (horizontalPosition) {
+      case ComputedHorizontalPosition.Left:
+        left -= extraOffsetLeft;
+        break;
+    }
+
+    position.style.top = top;
+    position.style.left = left;
+    position.style.width = width + extraOffsetLeft * 2;
+    position.style["min-width"] = `320px`;
+
+    return position;
+  }
+
   /**
    * A task that queries the server for people matching the given query.
    * Used as the `search` action for the `ember-power-select` component.
diff --git a/web/app/styles/components/multiselect.scss b/web/app/styles/components/multiselect.scss
index 0f52c9b5a..6f7dc98ec 100644
--- a/web/app/styles/components/multiselect.scss
+++ b/web/app/styles/components/multiselect.scss
@@ -37,11 +37,11 @@
   }
 
   .ember-power-select-multiple-options {
-    @apply flex flex-wrap h-full mr-6;
+    @apply mr-6 flex h-full flex-wrap gap-2.5;
   }
 
   .ember-power-select-trigger-multiple-input {
-    min-width: 80px;
+    @apply min-w-[80px] px-[3px] text-body-200 placeholder:text-color-foreground-disabled;
 
     &::-webkit-search-cancel-button {
       display: none;
@@ -49,10 +49,14 @@
   }
 
   .ember-power-select-multiple-option {
-    @apply flex items-center px-0 m-0.5 max-w-[100%] relative pr-7 pl-1.5 py-1 border-0;
+    @apply relative inline-flex max-w-full items-center border-0 text-color-foreground-strong;
+
+    // Compensate for the chip padding by setting negative margins.
+    // Allows content to maintain its position in both the edit and read-only states.
+    @apply -my-1 -ml-[3px] -mr-1 py-1 px-0 pl-[3px] pr-7;
 
     .ember-power-select-multiple-remove-btn {
-      @apply absolute right-1 grid place-items-center h-5 w-5 shrink-0 z-10 rounded-sm text-color-foreground-primary pb-px;
+      @apply absolute right-1 z-10 grid h-5 w-5 shrink-0 place-items-center rounded-sm pb-px text-color-foreground-primary;
 
       &:hover {
         @apply bg-neutral-200;
diff --git a/web/app/styles/components/sidebar.scss b/web/app/styles/components/sidebar.scss
index f993bbb1c..63ea0ad92 100644
--- a/web/app/styles/components/sidebar.scss
+++ b/web/app/styles/components/sidebar.scss
@@ -163,7 +163,7 @@
   }
 
   .person-list {
-    @apply w-full space-y-2;
+    @apply grid w-full gap-2.5;
   }
 
   .sidebar-footer {
diff --git a/web/app/styles/ember-power-select-theme.scss b/web/app/styles/ember-power-select-theme.scss
index a53a6580e..1f39e948d 100644
--- a/web/app/styles/ember-power-select-theme.scss
+++ b/web/app/styles/ember-power-select-theme.scss
@@ -1,6 +1,5 @@
-@import "ember-basic-dropdown";
+// https://github.com/cibernox/ember-power-select/blob/master/ember-power-select/scss/variables.scss
 
-// ember-power-select
 $ember-power-select-background-color: var(
   --token-form-control-base-surface-color-default
 );
@@ -10,8 +9,9 @@ $ember-power-select-disabled-background-color: var(
 $ember-power-select-multiple-selection-background-color: var(
   --token-color-palette-neutral-100
 );
+$ember-power-select-highlighted-color: inherit;
 $ember-power-select-highlighted-background: var(
-  --token-color-foreground-action
+  --token-color-surface-interactive-hover
 );
 $ember-power-select-border-color: var(
   --token-form-control-base-border-color-default
@@ -21,24 +21,53 @@ $ember-power-select-default-border: var(--token-form-control-border-width) solid
 $ember-power-select-default-border-radius: var(
   --token-form-control-border-radius
 );
+
+$ember-power-select-opened-border-radius: var(
+  --token-form-control-border-radius
+);
+
 $ember-power-select-focus-box-shadow: var(--token-elevation-low-box-shadow);
 $ember-power-select-dropdown-box-shadow: var(--token-elevation-low-box-shadow);
-$ember-power-select-option-padding: 7px; // Can't use --token-form-control-padding here.
+$ember-power-select-option-padding: 8px;
 $ember-power-select-focus-outline: 3px solid
   var(--token-color-focus-action-external);
-$ember-power-select-trigger-ltr-padding: var(--token-form-control-padding);
-$ember-power-select-trigger-rtl-padding: var(--token-form-control-padding);
-$ember-power-select-multiple-option-padding: 0 7px;
+$ember-power-select-trigger-ltr-padding: 7px 5px;
+$ember-power-select-trigger-rtl-padding: 7px 5px;
+$ember-power-select-multiple-option-padding: 0;
 $ember-power-select-multiple-option-line-height: 1.3;
 
 .ember-basic-dropdown-content {
-  .hds-dropdown-list-item--variant-interactive {
-    @apply flex items-center px-3;
+  @apply min-h-[34px];
 
-    &:hover {
-      @apply bg-color-surface-interactive-hover;
-    }
+  .hds-dropdown-list-item--variant-interactive {
+    @apply flex items-center px-2;
   }
 }
 
 @import "ember-power-select";
+
+.ember-basic-dropdown-content {
+  border: none !important;
+  @apply hds-surface-high mt-px;
+}
+
+.ember-power-select-options[role="listbox"] {
+  @apply max-h-[200px];
+}
+
+.ember-power-select-option {
+  @apply py-px;
+
+  &:first-child {
+    @apply mt-[3px];
+  }
+
+  &:last-child {
+    @apply mb-[3px];
+  }
+}
+
+.ember-power-select-option--loading-message,
+.ember-power-select-option--no-matches-message {
+  @apply h-7 px-3.5 text-color-foreground-faint;
+}
diff --git a/web/tests/integration/components/inputs/people-select-test.ts b/web/tests/integration/components/inputs/people-select-test.ts
index ba0af47c1..665331116 100644
--- a/web/tests/integration/components/inputs/people-select-test.ts
+++ b/web/tests/integration/components/inputs/people-select-test.ts
@@ -37,8 +37,7 @@ module("Integration | Component | inputs/people-select", function (hooks) {
 
     assert
       .dom(".ember-power-select-option")
-      .exists({ count: 1 })
-      .hasText("Type to search");
+      .doesNotExist('"Type to search" message is hidden');
 
     await fillIn(".ember-power-select-trigger-multiple-input", "u");
 
@@ -115,7 +114,7 @@ module("Integration | Component | inputs/people-select", function (hooks) {
 
     assert
       .dom(".ember-power-select-option--loading-message")
-      .hasText("Loading options...");
+      .hasText("Loading...");
 
     await fillInPromise;