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I've run into a few different cases now. For example this SMILES, taken from (PubChem CID:102301051) is supposed to be the E stereochemistry:
C/C(=C\C(=O)OC)/C1=CC=C(C=C1)C(C)(F)F
However, this is the image generated by SmilesDrawer, which is the wrong stereochemistry: