diff --git a/src/vs/editor/contrib/suggest/browser/suggestInlineCompletions.ts b/src/vs/editor/contrib/suggest/browser/suggestInlineCompletions.ts
index 060b60d499d..27d396e0b13 100644
--- a/src/vs/editor/contrib/suggest/browser/suggestInlineCompletions.ts
+++ b/src/vs/editor/contrib/suggest/browser/suggestInlineCompletions.ts
@@ -11,16 +11,16 @@ import { ICodeEditor } from 'vs/editor/browser/editorBrowser';
 import { registerEditorContribution } from 'vs/editor/browser/editorExtensions';
 import { ICodeEditorService } from 'vs/editor/browser/services/codeEditorService';
 import { EditorOption, FindComputedEditorOptionValueById } from 'vs/editor/common/config/editorOptions';
-import { Position } from 'vs/editor/common/core/position';
+import { IPosition, Position } from 'vs/editor/common/core/position';
 import { Range } from 'vs/editor/common/core/range';
 import { IWordAtPosition } from 'vs/editor/common/core/wordHelper';
 import { IEditorContribution } from 'vs/editor/common/editorCommon';
-import { InlineCompletion, InlineCompletionContext, InlineCompletions, InlineCompletionsProvider } from 'vs/editor/common/languages';
+import { CompletionItemProvider, CompletionTriggerKind, InlineCompletion, InlineCompletionContext, InlineCompletions, InlineCompletionsProvider } from 'vs/editor/common/languages';
 import { ITextModel } from 'vs/editor/common/model';
 import { ILanguageFeaturesService } from 'vs/editor/common/services/languageFeatures';
 import { CompletionItemInsertTextRule } from 'vs/editor/common/standalone/standaloneEnums';
 import { CompletionModel, LineContext } from 'vs/editor/contrib/suggest/browser/completionModel';
-import { CompletionItemModel, provideSuggestionItems, QuickSuggestionsOptions } from 'vs/editor/contrib/suggest/browser/suggest';
+import { CompletionItemModel, CompletionOptions, provideSuggestionItems, QuickSuggestionsOptions } from 'vs/editor/contrib/suggest/browser/suggest';
 import { ISuggestMemoryService } from 'vs/editor/contrib/suggest/browser/suggestMemory';
 import { WordDistance } from 'vs/editor/contrib/suggest/browser/wordDistance';
 import { IClipboardService } from 'vs/platform/clipboard/common/clipboardService';
@@ -114,15 +114,24 @@ class SuggestInlineCompletions implements InlineCompletionsProvider<InlineComple
 			return undefined;
 		}
 
-		const wordInfo = model.getWordAtPosition(position);
-		if (!wordInfo || wordInfo.word.length === 0 || wordInfo.endColumn !== position.column) {
-			// not without true prefix, not inside word
+
+		// We consider non-empty leading words and trigger characters. The latter only
+		// when no word is being typed (word characters superseed trigger characters)
+		let wordInfo = model.getWordUntilPosition(position);
+		let triggerCharacterInfo: { ch: string; providers: Set<CompletionItemProvider> } | undefined;
+
+		if (!wordInfo.word) {
+			triggerCharacterInfo = this._getTriggerCharacterInfo(model, position);
+		}
+
+		if (!wordInfo.word && !triggerCharacterInfo) {
+			// not at word, not a trigger character
 			return;
 		}
 
 		let result: InlineCompletionResults;
 		const leadingLineContents = model.getValueInRange(new Range(position.lineNumber, 1, position.lineNumber, position.column));
-		if (this._lastResult?.canBeReused(model, position.lineNumber, wordInfo)) {
+		if (!triggerCharacterInfo && this._lastResult?.canBeReused(model, position.lineNumber, wordInfo)) {
 			// reuse a previous result iff possible, only a refilter is needed
 			// TODO@jrieken this can be improved further and only incomplete results can be updated
 			// console.log(`REUSE with ${wordInfo.word}`);
@@ -136,8 +145,8 @@ class SuggestInlineCompletions implements InlineCompletionsProvider<InlineComple
 			const completions = await provideSuggestionItems(
 				this._languageFeatureService.completionProvider,
 				model, position,
-				undefined,
-				undefined,
+				new CompletionOptions(undefined, undefined, triggerCharacterInfo?.providers),
+				triggerCharacterInfo && { triggerKind: CompletionTriggerKind.TriggerCharacter, triggerCharacter: triggerCharacterInfo.ch },
 				token
 			);
 
@@ -165,6 +174,20 @@ class SuggestInlineCompletions implements InlineCompletionsProvider<InlineComple
 	freeInlineCompletions(result: InlineCompletionResults): void {
 		result.release();
 	}
+
+	private _getTriggerCharacterInfo(model: ITextModel, position: IPosition) {
+		const ch = model.getValueInRange(Range.fromPositions({ lineNumber: position.lineNumber, column: position.column - 1 }, position));
+		const providers = new Set<CompletionItemProvider>();
+		for (const provider of this._languageFeatureService.completionProvider.all(model)) {
+			if (provider.triggerCharacters?.includes(ch)) {
+				providers.add(provider);
+			}
+		}
+		if (providers.size === 0) {
+			return undefined;
+		}
+		return { providers, ch };
+	}
 }
 
 class EditorContribution implements IEditorContribution {