diff --git a/static/app/components/searchQueryBuilder/index.spec.tsx b/static/app/components/searchQueryBuilder/index.spec.tsx
index 9dcd04d4fb81..2d86a5bfabbf 100644
--- a/static/app/components/searchQueryBuilder/index.spec.tsx
+++ b/static/app/components/searchQueryBuilder/index.spec.tsx
@@ -8822,6 +8822,42 @@ describe('SearchQueryBuilder', () => {
         );
       });
     });
+
+    it('displays the pattern in the filter when the operator is matches regex', async () => {
+      render(
+        <SearchQueryBuilder
+          {...defaultProps}
+          allowRegexOperators
+          initialQuery="browser.name://fire.*fox//"
+        />
+      );
+
+      expect(
+        within(
+          await screen.findByRole('row', {name: 'browser.name://fire.*fox//'})
+        ).getByText('fire.*fox')
+      ).toBeInTheDocument();
+    });
+
+    it('displays the pattern over the input when editing a regex value', async () => {
+      render(
+        <SearchQueryBuilder
+          {...defaultProps}
+          allowRegexOperators
+          initialQuery="browser.name://fire.*fox//"
+        />
+      );
+      await userEvent.click(
+        screen.getByRole('button', {name: 'Edit value for filter: browser.name'})
+      );
+
+      expect(
+        await screen.findByRole('combobox', {name: 'Edit filter value'})
+      ).toHaveValue('fire.*fox');
+      expect(
+        screen.getByText('fire.*fox', {selector: '[aria-hidden="true"] *'})
+      ).toBeInTheDocument();
+    });
   });
 
   describe('regex pattern validation', () => {
diff --git a/static/app/components/searchQueryBuilder/tokens/combobox.tsx b/static/app/components/searchQueryBuilder/tokens/combobox.tsx
index e36f73d92136..5fb0b65c751e 100644
--- a/static/app/components/searchQueryBuilder/tokens/combobox.tsx
+++ b/static/app/components/searchQueryBuilder/tokens/combobox.tsx
@@ -121,6 +121,11 @@ type SearchQueryBuilderComboboxProps<T extends SelectOptionOrSectionWithKey<stri
   openOnFocus?: boolean;
   placeholder?: string;
   ref?: React.Ref<HTMLInputElement>;
+  /**
+   * Renders the input's value in an overlay drawn on top of the input, whose own
+   * text is hidden. Use to style the value beyond what an input can render.
+   */
+  renderInputValue?: (value: string) => ReactNode;
   /**
    * Function to determine whether the menu should close when interacting with
    * other elements.
@@ -421,6 +426,7 @@ export function SearchQueryBuilderCombobox<
   keepVisibleRef,
   'data-test-id': dataTestId,
   ref,
+  renderInputValue,
 }: SearchQueryBuilderComboboxProps<T>) {
   const {clearSearchQuery, dispatch} = useSearchQueryBuilderState();
   const {disabled} = useSearchQueryBuilderConfig();
@@ -666,55 +672,67 @@ export function SearchQueryBuilderCombobox<
 
   const autosizeInput = useAutosizeInput({value: inputValue});
 
-  return (
-    <Flex align="stretch" width="100%" height="100%" position="relative">
-      <UnstyledInput
-        {...inputProps}
-        size="md"
-        ref={mergeRefs(
-          ref,
-          inputRef,
-          autosizeInput,
-          triggerProps.ref as React.Ref<HTMLInputElement>
-        )}
-        type="text"
-        placeholder={placeholder}
-        onClick={handleInputClick}
-        value={inputValue}
-        onChange={handleInputChange}
-        tabIndex={tabIndex}
-        onPaste={onPaste}
-        disabled={disabled}
-        onKeyDownCapture={e => {
-          if (isCtrlKeyPressed(e) && (e.key === 'Backspace' || e.key === 'Delete')) {
-            if (token.type === Token.FREE_TEXT) {
-              e.preventDefault();
-              e.stopPropagation();
-              state.close();
-              dispatch({
-                type: 'DELETE_TO_CURSOR',
-                token,
-                cursorPosition: e.currentTarget.selectionStart ?? 0,
-                inputValue,
-                direction: e.key === 'Backspace' ? 'before' : 'after',
-              });
-              return;
-            }
-
-            if (!inputValue) {
-              e.preventDefault();
-              e.stopPropagation();
-              onSearchQueryClear?.();
-              state.close();
-              clearSearchQuery({reopenDropdown: true});
-              return;
-            }
+  const InputComponent = renderInputValue ? HighlightedInput : UnstyledInput;
+  const input = (
+    <InputComponent
+      {...inputProps}
+      size="md"
+      ref={mergeRefs(
+        ref,
+        inputRef,
+        autosizeInput,
+        triggerProps.ref as React.Ref<HTMLInputElement>
+      )}
+      type="text"
+      placeholder={placeholder}
+      onClick={handleInputClick}
+      value={inputValue}
+      onChange={handleInputChange}
+      tabIndex={tabIndex}
+      onPaste={onPaste}
+      disabled={disabled}
+      onKeyDownCapture={e => {
+        if (isCtrlKeyPressed(e) && (e.key === 'Backspace' || e.key === 'Delete')) {
+          if (token.type === Token.FREE_TEXT) {
+            e.preventDefault();
+            e.stopPropagation();
+            state.close();
+            dispatch({
+              type: 'DELETE_TO_CURSOR',
+              token,
+              cursorPosition: e.currentTarget.selectionStart ?? 0,
+              inputValue,
+              direction: e.key === 'Backspace' ? 'before' : 'after',
+            });
+            return;
           }
 
-          onKeyDownCapture?.(e, {state});
-        }}
-        data-test-id={dataTestId}
-      />
+          if (!inputValue) {
+            e.preventDefault();
+            e.stopPropagation();
+            onSearchQueryClear?.();
+            state.close();
+            clearSearchQuery({reopenDropdown: true});
+            return;
+          }
+        }
+
+        onKeyDownCapture?.(e, {state});
+      }}
+      data-test-id={dataTestId}
+    />
+  );
+
+  return (
+    <Flex align="stretch" width="100%" height="100%" position="relative">
+      {renderInputValue ? (
+        <HighlightStack>
+          {input}
+          <HighlightedValue aria-hidden>{renderInputValue(inputValue)}</HighlightedValue>
+        </HighlightStack>
+      ) : (
+        input
+      )}
       {description ? (
         <StyledPositionWrapper
           {...descriptionPopper.attributes.popper}
@@ -769,6 +787,37 @@ const UnstyledInput = styled(Input)`
   }
 `;
 
+// The input and its highlighted value share one grid cell at least as wide as the value's
+// text, so the input never scrolls its own text out from under the highlighting.
+const HighlightStack = styled('div')`
+  display: grid;
+  grid-template-columns: minmax(max-content, 1fr);
+  flex-grow: 1;
+`;
+
+// WebKit doesn't kern across the highlighted value's token spans, so neither side kerns.
+const HighlightedInput = styled(UnstyledInput)`
+  grid-area: 1 / 1;
+  min-width: 100%;
+  color: transparent;
+  caret-color: ${p => p.theme.tokens.content.primary};
+  font-kerning: none;
+  font-variant-ligatures: none;
+`;
+
+const HighlightedValue = styled('div')`
+  grid-area: 1 / 1;
+  align-self: center;
+  padding-right: ${p => p.theme.space['2xs']};
+  white-space: pre;
+  pointer-events: none;
+  font-family: ${p => p.theme.font.family.sans};
+  font-weight: ${p => p.theme.font.weight.sans.regular};
+  font-size: ${p => p.theme.form.md.fontSize};
+  font-kerning: none;
+  font-variant-ligatures: none;
+`;
+
 const StyledPositionWrapper = styled('div')<{visible?: boolean}>`
   display: ${p => (p.visible ? 'block' : 'none')};
   z-index: ${p => p.theme.zIndex.tooltip};
diff --git a/static/app/components/searchQueryBuilder/tokens/filter/filter.tsx b/static/app/components/searchQueryBuilder/tokens/filter/filter.tsx
index bf12b3b9071d..65ffb2b4a71f 100644
--- a/static/app/components/searchQueryBuilder/tokens/filter/filter.tsx
+++ b/static/app/components/searchQueryBuilder/tokens/filter/filter.tsx
@@ -22,6 +22,7 @@ import {
 import {AggregateKey} from 'sentry/components/searchQueryBuilder/tokens/filter/aggregateKey';
 import {FilterKey} from 'sentry/components/searchQueryBuilder/tokens/filter/filterKey';
 import {FilterOperator} from 'sentry/components/searchQueryBuilder/tokens/filter/filterOperator';
+import {renderRegexPattern} from 'sentry/components/searchQueryBuilder/tokens/filter/highlightedRegexPattern';
 import {UnstyledButton} from 'sentry/components/searchQueryBuilder/tokens/filter/unstyledButton';
 import {useFilterButtonProps} from 'sentry/components/searchQueryBuilder/tokens/filter/useFilterButtonProps';
 import {
@@ -38,7 +39,7 @@ import {
   type ParseResultToken,
   type TokenResult,
 } from 'sentry/components/searchSyntax/parser';
-import {getKeyName} from 'sentry/components/searchSyntax/utils';
+import {getKeyName, isRegexOperator} from 'sentry/components/searchSyntax/utils';
 import {isQueryBuilderPanelChrome} from 'sentry/components/tokenizedInput/token/comboBoxLayout';
 import {IconClose} from 'sentry/icons';
 import {t} from 'sentry/locale';
@@ -97,14 +98,18 @@ function fitMiddleEllipsisToElement(
     return value;
   }
 
-  const previousText = element.textContent;
   const previousWidth = element.style.width;
   const fallback = ellipsizeFilterValue(value, fallbackMaxLength, multi);
 
+  // Detaching and reattaching the same nodes keeps the references React holds valid.
+  // Writing `element.textContent` instead would destroy any rendered child elements.
+  const children = Array.from(element.childNodes);
+  const measureNode = document.createTextNode(value);
+
   try {
     // Expand to the full value first so content-sized ancestors can grow up to their
     // max-width when the window/search bar is no longer constraining them.
-    element.textContent = value;
+    element.replaceChildren(measureNode);
     element.style.width = '';
 
     if (element.clientWidth <= 0) {
@@ -124,13 +129,13 @@ function fitMiddleEllipsisToElement(
 
     let low = 1;
     let high = value.length;
-    element.textContent = ELLIPSIS;
+    measureNode.data = ELLIPSIS;
     let best = element.scrollWidth <= availableWidth ? ELLIPSIS : '';
 
     while (low <= high) {
       const mid = Math.floor((low + high) / 2);
       const candidate = ellipsizeFilterValue(value, mid, multi);
-      element.textContent = candidate;
+      measureNode.data = candidate;
       if (element.scrollWidth <= availableWidth) {
         best = candidate;
         low = mid + 1;
@@ -141,7 +146,7 @@ function fitMiddleEllipsisToElement(
 
     return best;
   } finally {
-    element.textContent = previousText;
+    element.replaceChildren(...children);
     element.style.width = previousWidth;
   }
 }
@@ -150,10 +155,12 @@ function TruncatedFilterDisplayValue({
   value,
   fallbackMaxLength,
   multi = false,
+  renderValue,
 }: {
   fallbackMaxLength: number;
   value: string;
   multi?: boolean;
+  renderValue?: (displayValue: string) => React.ReactNode;
 }) {
   const ref = useRef<HTMLDivElement>(null);
   const [displayValue, setDisplayValue] = useState(() =>
@@ -203,7 +210,7 @@ function TruncatedFilterDisplayValue({
 
   return (
     <Truncated ref={ref} data-overflowing={displayValue === value ? undefined : 'true'}>
-      {displayValue}
+      {renderValue ? renderValue(displayValue) : displayValue}
     </Truncated>
   );
 }
@@ -269,6 +276,7 @@ export function FilterValueText({token}: {token: TokenResult<Token.FILTER>}) {
         <TruncatedFilterDisplayValue
           value={formatFilterValue({token: token.value, valueType})}
           fallbackMaxLength={FILTER_VALUE_FALLBACK_MAX_LENGTH}
+          renderValue={isRegexOperator(token.operator) ? renderRegexPattern : undefined}
         />
       );
     }
diff --git a/static/app/components/searchQueryBuilder/tokens/filter/highlightedRegexPattern.spec.tsx b/static/app/components/searchQueryBuilder/tokens/filter/highlightedRegexPattern.spec.tsx
new file mode 100644
index 000000000000..091cd3e92794
--- /dev/null
+++ b/static/app/components/searchQueryBuilder/tokens/filter/highlightedRegexPattern.spec.tsx
@@ -0,0 +1,51 @@
+import {render, screen} from 'sentry-test/reactTestingLibrary';
+
+import {loadPrismLanguage} from '@sentry/scraps/code';
+
+import {renderRegexPattern} from 'sentry/components/searchQueryBuilder/tokens/filter/highlightedRegexPattern';
+
+jest.unmock('prismjs');
+
+describe('renderRegexPattern', () => {
+  beforeAll(async () => {
+    await loadPrismLanguage('regex', {});
+  });
+
+  it('marks up anchors, character sets, and quantifiers when given a pattern', () => {
+    render(renderRegexPattern('^GET /api/\\d+$'));
+
+    expect(screen.getByText('^')).toHaveClass('anchor');
+    expect(screen.getByText('GET /api/')).toBeInTheDocument();
+    expect(screen.getByText('\\d')).toHaveClass('char-set');
+    expect(screen.getByText('+')).toHaveClass('quantifier');
+    expect(screen.getByText('$')).toHaveClass('anchor');
+  });
+
+  it('marks up the brackets and range when given a character class', () => {
+    render(renderRegexPattern('[a-z]{2,3}'));
+
+    expect(screen.getByText('[')).toHaveClass('char-class-punctuation');
+    expect(screen.getByText('-')).toHaveClass('range-punctuation');
+    expect(screen.getByText(']')).toHaveClass('char-class-punctuation');
+    expect(screen.getByText('{2,3}')).toHaveClass('quantifier');
+  });
+
+  it('marks up the group and keeps the text when given a half-typed pattern', () => {
+    render(renderRegexPattern('(foo'));
+
+    expect(screen.getByText('(')).toHaveClass('group');
+    expect(screen.getByText('foo')).toBeInTheDocument();
+  });
+
+  it('keeps the ellipsis when given a middle-truncated pattern', () => {
+    render(renderRegexPattern('^abc…xyz$'));
+
+    expect(screen.getByText('abc…xyz')).toBeInTheDocument();
+  });
+
+  it('renders the text when given a pattern of only literals', () => {
+    render(renderRegexPattern('firefox'));
+
+    expect(screen.getByText('firefox')).toBeInTheDocument();
+  });
+});
diff --git a/static/app/components/searchQueryBuilder/tokens/filter/highlightedRegexPattern.tsx b/static/app/components/searchQueryBuilder/tokens/filter/highlightedRegexPattern.tsx
new file mode 100644
index 000000000000..993c65b5356a
--- /dev/null
+++ b/static/app/components/searchQueryBuilder/tokens/filter/highlightedRegexPattern.tsx
@@ -0,0 +1,44 @@
+import styled from '@emotion/styled';
+
+import {usePrismTokens} from 'sentry/utils/usePrismTokens';
+
+export const renderRegexPattern = (pattern: string) => (
+  <HighlightedRegexPattern pattern={pattern} />
+);
+
+function HighlightedRegexPattern({pattern}: {pattern: string}) {
+  const [tokens] = usePrismTokens({code: pattern, language: 'regex'});
+
+  return (
+    <PatternTokens>
+      {tokens?.length
+        ? tokens.map((token, index) => (
+            <span key={index} className={token.className}>
+              {token.children}
+            </span>
+          ))
+        : pattern}
+    </PatternTokens>
+  );
+}
+
+const PatternTokens = styled('span')`
+  color: ${p => p.theme.tokens.content.primary};
+
+  .token.group,
+  .token.quantifier,
+  .token.alternation,
+  .token.anchor,
+  .token.char-class-punctuation,
+  .token.char-class-negation,
+  .token.range-punctuation {
+    color: ${p => p.theme.tokens.syntax.operator};
+  }
+
+  .token.char-set,
+  .token.escape,
+  .token.special-escape {
+    color: ${p =>
+      p.theme.type === 'dark' ? p.theme.colors.green600 : p.theme.tokens.content.success};
+  }
+`;
diff --git a/static/app/components/searchQueryBuilder/tokens/filter/valueCombobox.tsx b/static/app/components/searchQueryBuilder/tokens/filter/valueCombobox.tsx
index c1d44ead6585..18253b0cb2ab 100644
--- a/static/app/components/searchQueryBuilder/tokens/filter/valueCombobox.tsx
+++ b/static/app/components/searchQueryBuilder/tokens/filter/valueCombobox.tsx
@@ -29,6 +29,7 @@ import {
   type CustomComboboxMenu,
   type CustomComboboxMenuProps,
 } from 'sentry/components/searchQueryBuilder/tokens/combobox';
+import {renderRegexPattern} from 'sentry/components/searchQueryBuilder/tokens/filter/highlightedRegexPattern';
 import {parseMultiSelectFilterValue} from 'sentry/components/searchQueryBuilder/tokens/filter/parsers/string/parser';
 import {SpecificDatePicker} from 'sentry/components/searchQueryBuilder/tokens/filter/specificDatePicker';
 import {useFrozenSuggestionSectionItems} from 'sentry/components/searchQueryBuilder/tokens/filter/useFrozenSuggestionSectionItems';
@@ -869,9 +870,14 @@ export function SearchQueryBuilderValueCombobox({
     // a long neighbouring chip can't keep it off-screen.
     const containerRect = container.getBoundingClientRect();
     const inputRect = input.getBoundingClientRect();
+    // An input wider than the row can't be brought fully into view.
+    const isWiderThanRow = inputRect.width > containerRect.width;
+    if (isWiderThanRow && input.selectionStart !== input.value.length) {
+      return;
+    }
     if (inputRect.right > containerRect.right) {
       container.scrollLeft += inputRect.right - containerRect.right;
-    } else if (inputRect.left < containerRect.left) {
+    } else if (inputRect.left < containerRect.left && !isWiderThanRow) {
       container.scrollLeft -= containerRect.left - inputRect.left;
     }
   }, []);
@@ -1424,6 +1430,7 @@ export function SearchQueryBuilderValueCombobox({
         inputValue={inputValue}
         filterValue={filterValue}
         placeholder={placeholder}
+        renderInputValue={isRegexValue ? renderRegexPattern : undefined}
         token={token}
         inputLabel={t('Edit filter value')}
         keepVisibleRef={ref}
@@ -1464,6 +1471,7 @@ export function SearchQueryBuilderValueCombobox({
     ? committedValues.filter(v => v.index < editingChip.index).length
     : chips.length;
   const chipRow = [...chips.slice(0, inputSlot), valueInput, ...chips.slice(inputSlot)];
+  const rowScrolls = canSelectMultipleValues || isRegexValue;
 
   return (
     <ValueComboboxContext.Provider value={valueComboboxContextValue}>
@@ -1473,8 +1481,8 @@ export function SearchQueryBuilderValueCombobox({
           gap="2xs"
           minWidth="0"
           height="100%"
-          overflowX={canSelectMultipleValues ? 'auto' : undefined}
-          overflowY={canSelectMultipleValues ? 'hidden' : undefined}
+          overflowX={rowScrolls ? 'auto' : undefined}
+          overflowY={rowScrolls ? 'hidden' : undefined}
           ref={ref}
           data-test-id="filter-value-editing"
         >